White steeples against crisp blue skies, glorious autumn colors and fall foliage like you wouldn’t believe, fresh lobster rolls, REAL maple syrup – New England conjures all kinds of cozy associations! And some not so cozy, like great white sharks, witch-hunts, whaling, and rabid sports fans (don’t worry, they don’t attack unless you’re wearing a Yankees hat). Whether you’re planning a fall getaway or a summer vacation, the coastline and mountains of New England make for one truly unforgettable road trip!
My family hails from New England as far back as the Mayflower, and for the first 3 years of my life, I was a full-fledged Bostonian – accent and all. I spent quite a bit of time visiting Massachusetts growing up: staying with family in Cape Cod, visiting my sister at college in Boston (Wellesley), briefly attending college in Western Massachusetts (Mount Holyoke), and interning for one sunny summer in Newburyport. But I’ve yet to complete a full-fledged New England road trip… which is why I tapped travel writer and Massachusetts local Anna Laird Barto to create the perfect itinerary!
This New England road trip itinerary visits Massachusetts, Maine, New Hampshire, Vermont, Connecticut, and Rhode Island and captures as much of New England’s charm, beauty, history and quirkiness as possible in ten days – with plenty of stops for witches, ghosts, and lobsters along the way. Take it away, Anna!
Psst: Planning on exploring more of the East Coast? Take a look at some of our other posts!
- 3 Days in Boston: The Ultimate Weekend Itinerary for Boston, Massachusetts
- 10 Charming Places to Experience Fall in New Hampshire
- 36 Things to do in Hudson Valley, New York: A Complete Local’s Guide
- The Ultimate Local’s Guide to Washington, DC
Psst: Planning a New England road trip? We’ve created a free, printable version of this itinerary! Plus, we’ll also send you our favorite tips to help you plan your road trip. Just sign up below.
New England Road Trip FAQs
Because the whole of New England is comparatively small – about the size of Arizona – outsiders often underestimate the diversity within the region. When I tell people out west I’m from Massachusetts, they immediately assume I’m from Boston.
Actually, my hometown of Amherst is closer to Vermont. And no one in this part of the state sounds like JFK or an Irish mobster from a Scorsese film. I like to think that we’re better drivers too.
Other than where you’ll find the worst drivers in New England (ahem: Boston), there are a few more things you’ll need to know before taking your New England road trip.
Where should I fly in and out of?
This itinerary starts and finishes in Boston. Boston Logan is one of the busiest airports in the country, with non-stop service to and from hundreds of destinations worldwide. It’s also just a 10-20 minute drive from downtown, depending, as always, on the traffic!
Where should I rent a car?
All the major car rental agencies operate out of Logan. But be forewarned that parking spaces are the most coveted real estate in the city. If you stay anywhere near downtown, you will pay to park, typically between $25-$39 per day.
Another option is to take a Lyft to your hotel and pick up your car the next morning, either at Logan or a downtown location. You won’t need or want a car to get around downtown.
- Travel Tip: Booked your flight and rental car yet? We recommend using Kayak to price-compare deals and dates to save money… so you can spend more on food during your trip (#letsbehonest).
What’s the best time of the year to take a New England Road Trip?
Go in the fall if you can, and prepare to be spoiled for fall anywhere else for the rest of your life. It’s not only about the leaves, which morph into every imaginable tone of gold, orange, red, and brown, but the crisp, clear air and the sun burning through the morning mist.
The farther north you go, the earlier the leaves change color, although the exact timing varies due to things like average annual rainfall and temperature. Generally, peak colors appear in Maine and northern New England around the end of September, while Connecticut may not see peak colors until almost Halloween.
If you can’t swing a fall trip, summer is a close second. The weather can be downright sultry, especially in southern New England, but the ocean, beaches, and spring-fed swimming holes are cold and refreshing! Plus, summer is the ideal time of year for a delicious lobster roll!
Things To Know Before Taking a New England Road Trip?
- In New England we have “highways” not “freeways.” We usually refer to them by number: 495, 91, etc., except for Route 90, which is simply “the Pike.” This itinerary avoids the Pike because it’s full of trucks and potholes.
- Watch for deer, moose… and wild turkeys! Flocks of wild turkeys are common even in the suburbs. When they decide to cross the road, spare your horn: no power on earth can make them hurry up.
- Drive times can vary dramatically depending on traffic, especially around Boston. We did warn you about the drivers in Boston, right?
- Don’t be fooled by our gruff exterior. New Englanders might not seem friendly, but we’re secretly dying to tell you all about this place we call home. Just don’t get my dad started on the geology of Cape Cod’s Kettle Lakes!
What’s the history of New England?
We all know the rather truncated and not-always-accurate version that we learned in school: in 1600-something, a bunch of English Puritans seeking religious freedom sailed across the sea in the Mayflower (along with Lia’s problematic ancestor, Miles Standish) and arrived at Plymouth Rock, some close to death and with absolutely no clue what they were doing. Thanks to the generosity of the Indigenous peoples, their ancestors, and millions of others who followed, they thrived enough to subsequently take over the entire continent. The rest – witch hunts and revolutions and all, see Hamilton and The Crucible for details – is history.
But what about the history of New England BEFORE the arrival of the Mayflower? Thousands of years before the US (much less the Red Sox) declared itself a nation, this northeastern tip of Turtle Island was cared for by the Nipmuc, Massachusetts, Mohegan, Mohican, Narraganset, Nauset, Niantic Schaghticoke, Pocumtuc, Pequot and Wampanoag nations, and the affiliated tribes of the Wabanaki Confederacy.
Today, New England’s Native peoples (yes, they’re still here!) identify as 16 distinct Nations and Tribes. They continue to hold their ground, despite ongoing challenges to their sovereignty, such as in 2020, when the US Department of Interior attempted to revoke the trust status of the Mashpee Wampanoag homelands.
The Ultimate New England Road Trip Itinerary
You’ll be driving a lot, but this itinerary makes a point of taking the scenic route, with frequent opportunities to stop in quaint small towns. Choosing which ones to feature is almost like choosing between my children, so if you have extra time, stay an extra night anywhere along the way!
Without further ado let’s get started on your New England road trip!
Day 1: a Proper Day in Boston, Massachusets
- Today you’ll get the most proper Boston experience possible in a single day.
- Drive Time: None. Fortunately, Boston is one of America’s “Most Walkable” cities, because it’s one of the worst places to drive, much less park. Besides, it wouldn’t be a Proper Boston experience without taking mass transit, better known as the “T.”
Ahhh, Beantown. Welcome to Bahstan: a city defined by its rich history and sports culture, full of homey, Cheers-esque bars and a thriving theater scene, with harbor views around every corner and a bustling city center that somehow feels both old and new at the same time.
There is no way to see everything in Boston one day, but with some smart planning, you can see a lot. My personal preference – more of a bias – is for the Italian North End and Charlestown, where I ran a community program for many years.
A good way to see a lot of sights in a short amount of time, especially if you’re tired from a long flight, is to squeeze it all in on a Duck Tour. The infamous Duck boat – a World War II-style amphibious vehicle – is a Boston icon in its own right! The 80-minute tour takes you past landmarks like Boston Common, Faneuil Hall, and Quincy Market, before plunging into the Charles River for a duck’s-eye view of the city skyline.
For lunch – or dinner, depending on when your flight gets in – head to the old Italian North End. Locals argue to the death about whether the pizza is better at Regina’s or Umberto’s, or if Modern Pastry or Mike’s has better cannolis. My favorite is whichever has the shortest line!
Follow the Freedom Trail (marked by a redbrick line) through the charming cobblestone alleys of the North End and across the bridge to Charlestown. Take in the view from the Bunker Hill Monument (actually on Breed’s Hill) before hitting Paul Revere’s favorite hangout, The Warren Tavern, for dinner and/or drinks.
- Tip: Watch Ben Affleck’s The Town for an action-packed but surprisingly complex introduction to Boston’s oldest neighborhood – plus a cameo by the owner of my favorite laundromat!
Where to Stay: The Harborside Inn offers the best value for the best location, a short walk from the harbor, duck tour, Freedom Trail, Quincy Market, and several T stops. Or, if you’re feeling adventurous, you can stay directly IN the harbor on a houseboat! (Feel free to pour a little tea over the side to really get in the spirit of things, too.)
Day 1 Summary
- Arrive at Logan International
- Eat Breakfast (any time) at The Friendly Toast
- Take a Boston Duck Tour
- Lunch or dinner at Galleria Umberto or Regina’s in the North End
- Follow the Freedom Trail to Bunker Hill Monument/Breed’s Hill in Charlestown
- Dinner or drinks at the Warren Tavern in Charlestown
- Stay at the Harborside Inn or a rent a houseboat in Boston Harbor
Day 2: Boston to Portland, Maine (with a spooky Salem stopover)
- Today you’ll head up the seacoast to Portland, Maine, stopping at the infamous town of Salem.
- Drive Time: 2-3 Hours
Before hitting the road, grab breakfast and gather provisions at the Boston Public Market, an indoor marketplace where you’ll find everything from maple bacon glazed donuts to Kelp Smoothies.
Now it’s on to Salem, about 40 minutes north via the Essex Coastal Scenic Byway (Route 127) which takes you through the elegant seaside communities of Swampscott and Marblehead. Unlike Boston, Salem has ample public parking, and all attractions are within easy walking distance.
If it weren’t for the 1692 Salem Witch Trials, Salem would be just another, albeit very lovely, North Shore port town. Instead, this small town is the global epicenter of all things occult.
In the 21st century Salem, it’s still hard to separate the history from the hype. My advice is to embrace the madness, which during the month of October is pretty much 24/7.
For a look behind the hype, sign up for Kenneth Glover’s Morning Stroll Historical Tour. Kenneth provides an overview of the Witch Trails AND Salem’s Native American and maritime history as you stroll through Salem’s narrow streets past 17th-century landmarks like the Salem Witch House and Hamilton Hall.
After lunch at the Lobster Shanty – famous for its “warm beer, lousy food, surly waitresses, rude bartenders, and cranky cooks” – immerse yourself in witch kitsch before hitting the road for the 1-2 hour drive to Portland. Get a psychic reading, stock up on spell-casting supplies, or visit the Salem Wax Museum.
If you have an extra day in Salem:
- Tour The House of the Seven Gables, the inspiration for Nathaniel Hawthorne’s 1851 novel of the same name, and one of the oldest wooden mansions in the US.
- Cross over to the dark side with the Salem Haunted History Night Walking Tour.
- Visit the Peabody Essex Museum, a world-class art museum which has nothing to do with witches, although it does feature early New England maritime art, along with other treasures from around the world.
Jump back on Route 127 until your bladder gives you an excuse to stop in Manchester-by-the-sea, Gloucester, Rockport or charming Newburyport. (Side note from Lia: Newburyport is gorgeous! I spent a happy summer here working at an internship on the harbor. Highly recommend a pit stop!)
Say hello to New Hampshire for a hot second (don’t worry, you’ll be back) before arriving in Portland, Maine, in what was once the heart of the Wabanaki Confederacy. The drive from Salem to Portland is about an hour and forty minutes.
Portland, Maine, is the older, colder – wiser? – cousin of Portland, Oregon. Like their west coast counterparts, Portland Mainers are passionate about art, the outdoors, and their local microbrews, which you’ll have the opportunity to sample.
But first, stop in at the International Cryptozoology Museum, because what better way to get into the mood for the Maine Woods than learning about big hairy cryptids? Notable exhibitions include Bigfoot hairs and Abominable Snowman scat. You can also pick up a Santa Yeti Christmas ornament for mom at the CryptoStore!
By now, you probably need a drink, so it’s on to Allagash, Austin Street, and/or another of Portland’s local breweries for a palate-cleansing flight of beer or cider, before chowing down on some nouveau, New England food at Central Provisions.
Where to Stay: You probably won’t be spending much time at the hotel, but the Inn at St John offers clean, quaint accommodations at affordable rates. Or choose one of the fancier West End B&Bs like Chadwick’s.
Day 2 Summary
- Eat Breakfast at Boston Public Market
- Drive to Salem
- Morning Stroll Historical Tour
- Lunch at the The Lobster Shanty
- Explore your inner witchy side
- Drive to Portland
- Beer flights at Austin Street Brewery or Allagash
- Dinner at Central Provisions
- Stay at Inn at St John or Chadwick B&B
Day 3: Scenic Drive through Maine to Acadia
- Head down east along coastal Route 1 to Bar Harbor, stopping for lunch at McLoons Lobster Shack.
- Drive Time: 2.5-3 hours
Even if you ate breakfast at your B&B, you should still stop at Tandem Coffee Roasters on your way out of town. You can’t fill up the car at this converted ‘60s gas station, but you can refuel on single-origin coffee, cinnamon buns and yummy scones!
Maine has about 3,478 miles of coastline, more than California (just more squiggly), and today you’re going to see a lot of it: waves crashing on rocky beaches, sailboat-studded bays, Hallmark villages and scenic lighthouses.
Take a detour down Route 130 to the Pemaquid Point Lighthouse, about 40 minutes round-trip, perched dramatically atop a layer cake of metamorphosed rock.
We promised lobster, and it’s time to cash in in the state where it’s the most fresh and most inexpensive! Stop for lunch at an authentic Maine lobster shack, like the (deservedly) famous McCloon’s Lobster Shack in South Thomaston and Claws in Rockland, about an hour-and-a-half from Portland. These quirky roadside stands generally close for the season around the end of September – check the websites for exact dates. But fall road-trippers are in luck: an exception is Hazel’s Takeout in Rockland, which stays open until November.
While you’re in Rockland, check out the Archipelago, a store that supports artists and makers from Maine’s small coastal and island communities.
Continue on Route 1 through historic downtown Camden. Stop just up the road at Camden Hills State Park. Drive or walk to the top of Mount Battie for views of Camden Penobscot Bay and islands; views that inspired the poem “Renascence,” by Edna St. Vincent Millay.
From here it’s about an hour-and-forty-five minute drive to the stunning Acadia National Park, the jewel of Maine and arguably the best National Park on the Eastern seaboard! You’ll be exploring tomorrow, so check into your hotel and head to dinner.
For dinner, we recommend Side Street Cafe, a less touristy spot by Bar Harbor standards. It serves a variety of all-American fare but it’s best known for lobster rolls and blueberry pies, not to mention blueberry margaritas and blueberry ale.
Where to Stay: The closest town to the park is Bar Harbor. The charming Moseley Cottage Inn is the sweetest, most charming little quintessential New England B&B, and the Bar Harbor Inn & Spa is a more upscale boutique hotel.
Hotels here can be pricey, but there are some affordable, no-frills options. Many visitors to Acadia choose to camp instead. We know it’s hard to pack camping gear in your suitcase, so we found something even better – glamping! Reserve a safari-style A-frame tent in Lamoine, about thirty minutes north of the park. This private bay retreat comes with a solar shower, portable camp toilet and propane heater for cool fall nights.
Day 3 Summary:
- Breakfast at Tandem Coffee Roasters
- Stop at Pemaquid Point Lighthouse in Bristol
- Lunch at McCloon’s Lobster Shack in South Thomaston
- Stop to shop at Archipelago in downtown Rockland
- Take in the view at Camden Hills State Park
- Drive to Bar Harbor
- Dinner at Side Street Cafe
- Stay at the Moseley Cottage Inn, the Bar Harbor Inn & Spa, or glamp in Lamoine
Day 4: Bar Harbor and Acadia National Park, Maine
- Today you’ll experience one of America’s most magnificent national parks.
- Drive time: 0-3 hours, mostly within Acadia National Park
Route 1 was only a scenic warm-up! To experience Acadia National Park is to step back in geologic time – mountains split by receding glaciers, waves crashing in echo chambers of volcanic rock, spruce-covered islets and endless deciduous forest that bursts into color each fall.
This is the sacred landscape of the Wabanaki people, who still come here to harvest sweetgrass and go hiking!
The best way to appreciate Acadia is to hike the trails. If you have an extra day or two, this is a great way to spend them. However, the park also has shorter trails that fit into any itinerary, including this one.
Head out early and grab breakfast (to-go or at one of their picnic tables) from Hull’s Cove General Store. You can also pick up snacks and picnic supplies; they have a full-service deli, baked goods, pizza, and convenience store items.
After lunch, keep hiking, or tour park highlights. Ride the shuttle or take a self-guided driving tour of the park (approximately three hours) culminating with mind-blowing views from Mount Cadillac. If possible, time your trip so that you can watch the sunset from the summit.
Day 4 Summary:
- Breakfast at Hulls Cove General Store
- Hiking in Acadia National Park
- Picnic lunch or Jordan Pond House
- Self-Guided Driving Tour of Acadia National Park
- Dinner at Thirsty Whale Tavern or Acadia Lobster and BBQ
- Stay at the Moseley Cottage Inn, the Bar Harbor Inn & Spa, or glamp in Lamoine
Day 5: Maine to New Hampshire, the Northeast Kingdom
- Today’s drive takes you west along the Androscoggin River through the town of Bethel and up into the stunning White Mountains of New Hampshire!
- Drive time: 4.5 hours
Start with a hearty Great Maine Breakfast before heading north and west to Bethel via Route 2, about a four-hour drive. Take a short detour to see the Sunday River Covered Bridge in Newry. If the weathered truss bridge looks familiar, that’s because it is; the Sunday River Bridge is also known as the “Artist’s Bridge,” because it’s said to be the most painted and photographed bridge in the world.
Eat lunch and stock up on snacks at Good Food Bethel, which is – no kidding – a coffee shop, health food store, delicatessen, liquor store, AND BBQ joint in one.
After lunch, check out the Maine Mineral & Gem Museum, home of the 5 largest pieces of the Moon on Earth. They recently installed the largest single piece of Mars known to exist on Earth!
Take the rest of the afternoon to go raspberry picking (if you’re there in July) or apple picking (in September) at Gibson’s Apple Orchard. The orchard store is open until around Thanksgiving, selling homemade cider, local honey and maple syrup, so it’s worth a stop on a fall day!
From here it’s only a 30-minute drive to Gorham, New Hampshire, your base for exploring the White Mountains. You’ll notice the spine of the Carter-Moriah range rising to the southwest.
As you cross over the New Hampshire border, you’ll see a proliferation of billboards advertising things like alcohol and cigarettes. New Hampshire is the “Live Free or Die” state, and naturally death is preferable to paying sales tax… or wearing a helmet while riding a motorcycle.
For dinner in Gorham try The Notch Grille at The Glen House Hotel, where the only thing better than the food is the views. Floor to ceiling windows face the Presidential Range, evergreen slopes giving way to granite escarpments blanketed with snow for most of the year.
In the Algonquin language, these mountains are known as Wobanadenock, “the place of the high white or crystal/mica mountains.” The tallest of these peaks, often shrouded in clouds, is Mount Washington, home of some of the highest wind speeds on earth – that’s where you’re going tomorrow!
Where to Stay: Stay at The Glen House: If those firepits on the deck with sweeping mountain views don’t do it for you, perhaps the complimentary breakfast and cookies will! Or lean into the log cabins/alpine chalet vibe and stay at this stunning vacation rental, with incredible views, a super-modern kitchen, and a huge stone fireplace!
Day 5 Summary:
- Breakfast at Great Maine Breakfast
- Detour to the Sunday River Covered Bridge
- Get lunch at Good Food Bethel
- See the Moon meteorite at Maine Mineral & Gem Museum
- Drive to Gorham, New Hampshire
- Dinner at The Notch Grille
- Stay at The Glen House or an alpine chalet/cabin
Day 6: New Hampshire to Vermont (the White Mountains to the Green Mountains)
- Today you’ll climb Mount Washington and traverse the Kancamagus Scenic Byway on your way to the Green Mountains of Vermont.
- Drive Time: 2.5 hours
Eat breakfast at the homey White Mountain Cafe and Bookstore, where you can also pick up trail maps and local interest books.
By now you may have noticed the bumper stickers: “This Car Climbed Mount Washington.” Unless you have a whole day, and are a seasoned mountaineer, the best way to climb New England’s highest peak is via the auto road! (And then you can pick up a bumper sticker, too!)
The narrow, two-lane autoroad, completed in 1864, ascends 6,145 ft through a series of steep switchbacks. There are NO guardrails. If this is too much for you, no shame. Sign up for the guided tour, and let someone else do the driving.
The round-trip lasts about three hours, taking you from the leafy hardwood forest through boreal groves of evergreens and birch, gnarled conifers and blueberries, before emerging onto windswept alpine tundra. Most of the year, the summit is snowy, with thrilling views of nearby peaks poking up through the clouds.
At 6,145 feet, Mount Washington may seem puny compared to peaks out west, but don’t be fooled — due to its location at the intersection of storm tracks from the south and west, the summit experiences some of the most extreme weather conditions on earth. Winds as high as 230 mph have been recorded at the Mount Washington Observatory. You can be reassured that the auto road will be closed if conditions even remotely approach that.
If you want to forgo being in a car altogether, you can take the iconic Mount Washington Cog Railway to the top, which was the first mountain-climbing cog railway ever built. Opening in 1868, the biodiesel and steam train takes about three hours round-trip. At the summit, you can pick out a souvenir at the Sherman Adams Summit Building and visit the Tip Top House, a former hotel dating back to the 19th century that was turned into a historic site. It’s worth noting that from Oct. 18 to 31, there’s a special train that takes you to the north and east of the mountain.
After your mountain excursion, enjoy some classy comfort food on the four-season porch at the Wildcat Inn and Tavern in Jackson. After lunch, it’s time to hit “Kanc,” or Kancamagus Scenic Byway, which cuts through the heart of the White Mountain National Forest. It’s only about an hour and forty-minute drive from Jackson to Littleton, but leave more time, because there’ll be lots of opportunities to stop and ooh and ahh over the foliage, take a short hike, or check some more covered bridges off your list.
Last stop in New Hampshire is Littleton, a charming mill town that often flies under the tourist radar. Grab a beverage or snack at the Inkwell Coffee & Tea House or simply stretch your legs along the half-mile Riverwalk.
- Psst: Several of these stops – and a whole bunch more – are covered in our guide to fall in New Hampshire! New Hampshire is small enough to base yourself in one spot and take scenic drives to see the rest of the state, so if you feel like spending a few extra days in the White Mountains, head over to that post for more travel tips.
It’s time to leave stunning New Hampshire and dive into charming, beautiful Vermont. From Littleton, follow Route 2 east to the “NEK” – North East Kingdom of Vermont – land of mountains, lakes, small farms, and ICE CREAM.
That’s right: you can’t go to Vermont without making a pilgrimage to the ice-cream shrine of Ben & Jerry’s in Waterbury (about an hour and a half drive from Littleton). Take a Factory Tour and visit the Scoop Shop, serving classics like “Cherry Garcia,” as well as blasphemous new “Netflix Original Flavors” like “Netflix & Chilll’d.” While “Netflix & Chilll’d” is a permanent flavor, the other “Netflix Original Flavors” are being phased. Make sure to also check out Scoop Shop only flavors that can only be found there!
Drive twenty minutes north to the village of Stowe, where you’ll be staying tonight! This ski resort destination hangs onto its small-town charm, with a lively main street anchored by an iconic steepled church and local businesses like Laughing Moon Chocolates and Shaw’s General Store.
For dinner, head to Stowe’s hippest pizza place, The Deep End, where you order a drink from the refurbished airstream bar!
Where to Stay: Book a room at the Timberholm Inn, a cozy bed and breakfast overlooking the mountains.
Day 5 Summary:
- Breakfast at White Mountain Cafe and Bookstore
- Mount Washington Auto Road
- Lunch at Wildcat Tavern in Jackson
- Drive the Kancamagus Scenic Byway
- Stop in Littleton, New Hampshire
- Drive to Waterbury, Vermont
- Go for ice cream at the original Ben &Jerry’s
- Stay at the Timberholm Inn in Stowe
- Dinner at The Deep End
Day 7: The Two Faces of the Berkshires
- Today, you’ll take the back roads to the Berkshires through the Green Mountain National Forest, stopping at MASS MoCa in North Adams, Massachusetts.
- Drive Time: 3.5 hours
Start with breakfast at The Skinny Pancake, a Vermont chain that’s actually better known for its sweet and savory crepes featuring ingredients like maple pulled pork, local cranberry compote, and hazelnut spread.
From Stowe, take Route 7 south. You’ll stay on 7 for the next three hours. For most of the way, 7 is a rural, two-lane highway, winding through quintessential Vermont countryside: red barns, dairy cattle, and rolling green mountains. You know, typical jaw-dropping New England scenery.
Arriving in North Adams, just over the Massachusetts border, you’ll see another side of New England: a former industrial town that’s reinventing itself as an arts center.
Eat lunch at Lickety Split, a family-run eatery and ice cream parlor at the Massachusetts Museum of Contemporary Art (MASS MoCA). The menu is simple – soups, salads, quiches and sandwiches – but made from the freshest locally-sourced ingredients. The ice cream is also made in-house, using flavoring techniques pioneered by Ben & Jerry’s rival Steve Herrell.
The museum has transformed an abandoned brick factory complex into a multi-media art space. The football-field-sized Building 5 houses epic installations, like Glen Kaino’s “In the Light of Shadows,” in which thousands of suspended metal shards project otherworldly patterns of light across the vast warehouse space.
Now it’s on to the Berkshires. Just an hour’s drive south lies the playground of rich Manhattanites. You can hardly blame them: southwestern Massachusetts is both culturally rich and classically scenic.
Nowhere is this better epitomized than at The Mount, the sprawling romantic estate of author Edith Wharton. House tours end at 5pm, but the grounds of the 1902 mansion are open free from dawn until dusk.
Wander freely around the extensive gardens designed by Wharton herself, inspired by her travels to France and Italy. If you’re left wanting more, return after dinner for a ghost tour of the property, which has been featured in multiple episodes of Ghost Hunters.
Stay at the historic Church Street Inn in downtown Lenox, steps from trendy restaurants like Alta, a Mediterranean-style cafe and wine bar, where you can dine alfresco and watch the beautiful people – and tired tourists – pass.
Day 7 Summary:
- Breakfast at The Skinny Pancake in Stowe
- Drive to MASS MoCa North Adams
- Lunch Lickety Split Mass MoCA
- MASS MoCA
- Drive to Lenox, to The Mount
- Stay at the Church Street Inn
- Dinner at Alta
Day 8: Connecticut, Rhode Island, & Cape Cod
- Today you’ll pass through three different states on your way to Cape Cod, stopping for lunch and scenery on the Connecticut coast and Newport, Rhode Island.
- Drive Time: 5.5 hour
Eat breakfast on the porch at Ophelia’s, the Church Street Inn’s own restaurant, where the menu ranges from huevos rancheros to lemon ricotta pancakes with blueberry compote and – of course – local maple syrup. (If you must have Aunt Jemimah’s, hide it in your purse).
Today you’ll be covering a lot of ground, but it’s beautiful ground. Ignore all those signs for the Mass Pike and stay on Route 7 through Stockbridge and Great Barrington. You’ll stay on Route 7 for the next hour, before cutting through Litchfield Hill to Torrington.
From there, it’s about another hour and forty-five minutes to the coast. No, this isn’t the most direct route, but trust me, it’s much prettier than the 91 corridor and well worth the detour.
Now that you’ve dined in style, you’re ready to enter Newport high society. Set your own pace on this 1-2 hour Self-guided Driving Tour, which takes you past the “summer cottages” – AKA gilded age mansions – of the rich and famous.
From here, it’s a little over an hour (if the traffic Gods are smiling) to your penultimate destination: Cape Cod!
For the next two nights, rent a beach cottage in East Sandwich, complete sweeping ocean views, hammocks, and your very own private beach access. Take a sunset walk along the white sand beach before enjoying dockside boat-to-table cuisine at Fisherman’s View.
Day 8 Summary:
- Breakfast at the Inn restaurant, Ophelia’s
- Drive to Mystic via the Litchfield Hills
- Lunch at Mystic Pizza or Kamp Dog
- Newport scenic self driving tour
- Drive to Sandwich, Massachusetts on Cape Cod
- Dinner at Fisherman’s View
- Stay at a cottage on the beach
Day 9: Cape Cod Magic
- Rest and play on the lower Cape.
- Drive Time: 0-1 hour
You’ve been on the road for over a week. You’ve earned a rest, and what better place for it than Cape Cod, the flexed arm of Massachusetts.
Sandwich may be just over the bridge from the “mainland,” but it’s quintessentially Cape Cod, with its sandy beaches, salt marshes, lighthouses, and cottages with weathered grey shingles.
Sleep in as late as you want, then grab breakfast at Cafe Riverview, a popular spot staffed by students from the local high school.
After breakfast, spend the morning hanging out out on the beach. Sandwich is located on the Bay side of Cape Cod, so the waves are calm. The beaches are sheltered by sand dunes covered in long waving grasses, which fade to pale straw in autumn.
Walk the Sandwich Boardwalk while you can. The 100+ year plank bridge, which extends 1300 feet across the salt marsh to Cape Cod Bay, is set to be demolished soon and replaced with something uglier and more structurally sound.
Eat lunch at Cafe Chew, “Sandwich’s Sandwichery.” I don’t know what the Earl of Sandwich (alleged inventor of the sandwich) would make of their “Oatsy-Groatsy” sandwich with cucumber, baby spinach, tomato, feta cheese, pureed red pepper, caramelized onion, and hummus in a whole wheat wrap, but it sounds good to me.
Stroll the Sandwich Historic District for a last glimpse of the 16th century before returning to modernity. Tour the interiors of Cape Cod’s oldest homes, the Hoxie House and the Wing Fort House. They are currently closed due to the pandemic, but you can still appreciate the post-medieval timber frame construction, with uneven “saltbox” shaped roofs from the outside.
The irresistibly photogenic Dexter Grist Mill, built in 1654, overlooks Lower Shawme Pond, which is shaded by weeping willow trees and home to families of ducks and swans. The mill still operates, and from May through September you can purchase a bag of its fresh-ground cornmeal.
At last, it’s time to strap on your bib for a final feast of fried seafood and butter-drenched lobster at Mattakeese Wharf.
Day 9 Summary:
- Breakfast at Cafe Riverview
- Relax on East Sandwich Beach
- Walk to the plank, or Sandwich Boardwalk
- Sandwiches at Cafe Chew
- Explore Sandwich Historic District
- Last New England supper at Mattakeese Wharf
- Stay at a cottage on the beach
Day 10: Returning Home
- Complete the circle (blob?) back to Boston. If you have time, stop by in the famous town of Plymouth. Drop off your rental car and catch your flight home!
- Drive Time: 1.5-2 hours
Though it’s your last day, it doesn’t mean that you can’t squeeze a bit more New England history in (if your flight time allows, that is!).
Before you leave Cape Cod, eat a classic Ameican breakfast at 6a Cafe then hop on the road towards Plymouth.
Plymouth, Massachusetts, of course, is where the Mayflower Pilgrims landed in 1620 and the “new world” was born (at least to British folks—America was already inhabited). For good or ill, Plymouth was the first colony established by the pilgrims, and it holds one of the top spots in American lore.
A natural first stop is the Plymouth Rock, a many-ton hunk of granite that has diminished in size since 1620 due to its peregrinations and souvenir seeking, was identified as the spot of the Mayflower landing in 1741, 121 years after the fact.
While you’re in the area, you can check out the reproduction ship the “Mayflower II“, as well as Historic Patuxet, where Native Peoples lived for 12,000 years before being their numbers being severely reduced by an epidemic. You can also visit the Plimoth Patuxet Museums’ English Village, to see how the Pilgrims worked and lived. The entire museum complex is immersive with actors in period costumes, and you could easily spend the whole day learning about the people who once lived in the area.
- Side Note: At the Plimoth Patuxet Museums you may get a chance to meet Lia’s problematic ancestor, Miles Standish. Captain Miles Standish was the military leader of the Pilgrams, and was also the only person on the Mayflower to be openly non-religious – as there is no record that he ever joined the church. Why is he problematic, you ask? Well, as military leader of the Pilgrims, he fractured relations between the Pilgrims and the Indigenous peoples by violently attacking them without just cause. While this didn’t directly dissolve peace between the Pilgrims and the Indigenous peoples, I think it likely started the ball rolling down a path that would eventually lead to the almost complete genocide of the Native Americans. So. Big yikes.
For a bite for lunch before you head to the airport, check out Dillon’s Local in Plymouth. You can’t go wrong with their fish & chips or Cape Cod Reuben!
And then, it’s time to head back to Boston to catch your flight. Boston is 45 minutes to an hour away from Plymouth, but make sure to leave plenty of time before your flight because traffic is unpredictable!
What to Pack for a New England Road Trip
One thing people either adore or despise about New England is that we have very distinct seasons. You’ll need to pack accordingly!
- Layers: In the fall, the evenings and mornings can get very chilly, while daytime can be quite comfortable. Pack long and short sleeves, and thin sweaters that can fit easily under a fleece jacket or wool coat; that’s unless you’re from Arizona, or planning to hike Mount Washington, then you might also want one of these packable down jackets. And be sure to pack a few cute hats, scarves, and gloves for maximium fall cuteness and coziness! In the summer, you probably won’t need more than a hoodie at night, but bring a fleece jacket and windbreaker for the mountains.
- Bathing suit: You’ll be getting some good beach time on this road trip! But consider a wetsuit if you’re planning on spending any serious time in the ocean. Even in summer, average water temperatures remain in the 60s.
- Tevas or sneakers: You’ll want close-toed shoes for walking along rocky beaches.
- Umbrella and rain jacket: We’re prone to 1-3 day stretches of rainy weather any time, and hot summer days can produce explosive pop up thunderstorms.
- Mosquito and tick repellent: The most dangerous animal in New England is not the moose, or even the great white shark, but the mighty deer tick. Thanks to the deer tick, which is no larger than a sesame seed, New England has the nation’s highest rate of lyme disease. Pack a pair of pointy tweezers for safely removing a tick once it has embedded in your skin. But if it makes you feel better, I’ve lived in New England most of my life and I’ve never once had to do this.
- Hiking gear: You don’t need to go crazy at LL Bean, but you’ll want trail sneakers or hiking boots; long, lightweight pants (because of the ticks), and a small day pack for water, snacks, etc.
10-Day New England Road Trip Map
We’ve created a map of this New England road trip! It includes the itinerary highlights (i.e. where you will be driving to and staying) as well as the general driving directions (which include other locations just so Google will take you the right route). Save it for offline use in case your internet or GPS cuts out. And be sure to bookmark this page to refer back to while you’re planning!
About Our Contributor: Anna Laird Barto is a freelance writer who has lived everywhere from Cuba to Wisconsin but is now based in the wild west of Massachusetts. Her writing has appeared in a variety of travel, health, and literary magazines including Fodor’s, Hobart and Wanderlust. She supports her writing habit by working at a non-profit family center. To read more of her work visit annalairdbarto.com.
Are you ready to hit the road? Which stop on this New England road trip itinerary are you most excited about? Let us know in the comments below
Psst: Planning some East Coast getaways? Take a look at some of our other posts!
- 10 Magical Things To Do in Washington DC in the Winter
- 10 Charming Places to Experience Fall in New Hampshire
- The Ultimate Self-Guided Walking Tour of Lower Manhattan, NYC
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