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Amy Hartle

Amy Hartle is the Founder and Editor-in-Chief of New England With Love, a comprehensive resource for travel in the New England region. Amy has been exploring beautiful New England for more than 20 years, and has lived in both Vermont and New Hampshire, where she graduated from Plymouth State University. Amy has been a travel writer for more than a decade. On this site, Amy aims to share her love of New England and help you to find and experience the best adventures in all six states.

New England Road Trip FAQ

When’s the best time of year to road trip New England?

New England is gorgeous in all seasons, but for the easiest driving (and best New England road tripping experiences), summer and fall are ideal.

If you want the fall foliage experience, late September and early October are the key weeks to plan for. Of course, these times of years are also peak tourist season, so expect more traffic and higher hotel prices.

(PS: If you want to do a shorter road trip or a route that’s perfect for fall, check out my 7 day New England Fall Road Trip itinerary!

One of my favorite times of the year in New England is mid to late May. The weather is beautiful, and the region’s roads and attractions are generally less busy. The budding greenery is especially gorgeous and fresh, too.

Early September can also be lovely, just after kids have returned to school and summer has ended. Expect crisp temperatures and leaves just beginning to change colors.

A winter road trip may be doable, but remember, New England can be quite snowy, so you’ll want to have a reliable vehicle outfitted with snow tires, and you’ll need to stay aware of changing weather conditions and road closures.

How many days do you need for a road trip to New England?

You need 2-3 weeks for a comprehensive road trip around New England. This is the ideal amount of time needed to cover the major highlights of all six New England states.

If you don’t have that much time, you can still pack a lot into a shorter trip. A minimum of 7 to 10 days is ideal for a thorough yet relaxed New England road trip. For a 7-10 day trip, consider my Southern or Northern New England itineraries, or do shorter segments of the full 2-3 week itinerary.

Where should I start my road trip through New England?

I’ve started this New England travel itinerary in Boston, as it’s the biggest city in New England and home to a major airport, Boston Logan International. This airport is easy to fly into and rent a vehicle. Boston is also a great destination on its own, so my itinerary includes a couple days exploring the city.

Ps: Ready to rent a car for your New England drive? Click here to find the best rates on rental cars!

The Perfect New England Road Trip Itinerary

Days 1 & 2: Boston, Massachusetts

A street view in Boston, capturing the essence of a New England road trip itinerary, with cobblestone streets and historic brownstone buildings, featuring distinctive green bay windows. The scene is set against a backdrop of modern skyscrapers, merging the old with the new in this iconic cityscape. — *Boston is an excellent spot to start your New England tour!*

You’ll start your New England excursion from Boston, Massachusetts: an absolutely fantastic city.

Boston is a well-known place that’s filled to the brim with history. From famous historical events like the Boston Tea Party to its reputation as a modern-day sports town, you’ll never be bored here.

Some great things to do in Boston:

Visit the North End and dine on amazing Italian food. Don’t miss grabbing cannoli from Mike’s Pastry and Modern Pastry.
Stroll around quaint Beacon Hill
Tempt your taste buds with a Boston Food Tour
Go shopping on classy Newbury Street
Follow the Freedom Trail to learn Boston’s revolutionary history
Join an expert-led walking tour for a more in-depth experience of the city
Check out one of the many great Boston museums, including the Museum of Science which I especially love
Join a Boston Duck Tour and ride in one of the famous amphibious vehicles

Hotel Suggestion in Boston: Fairmont Copley Plaza

Need more guidance for Boston? Check out my post on The Top Things to Do in Boston for first timers, and I’ve also got some recommendations on where to grab coffee, breakfast, a beer, or a bite to eat in Boston, too!

PS: Looking for a shorter road trip from Boston? Check out my New England trip itinerary focusing on the journey from Boston to Acadia National Park.

Days 3 & 4: Newport, Rhode Island

amy standing in a black fur coat in front of a shop with a sign that says Coffee Grinder — *Was a cold day on this visit to Newport!*

On Day 3, drive from Boston to Newport. This is a straightforward route, with about 2 hours of drive time.

Glitz and glamour. That’s what you’ll find in Newport, Rhode Island. This town is perhaps best known for its iconic Gilded Age mansions . These opulent buildings were once the summer cottages of America’s rich and famous families.

Today, many of them have been converted into museums that you can wander through and admire some of New England’s opulence past.

Some of my favorite things to do in Newport:

Visit a mansion or two. I recommend The Breakers if you only have time for one of Newport’s mansions
Hop on this fun Gilded Age Mansions Tour, which takes you around via trolley
Stroll along the scenic Cliff Walk
Dine at the White Horse Tavern, America’s oldest operating restaurant

Hotel Suggestion in Newport: Hotel Viking

For further Newport ideas: Click here to read more about the top things to do in Newport, including beaches, restaurants, hotels, and vacation rentals too!

Day 5: Mystic, Connecticut

two white adirondack chairs face a calm river in mystic CT

Mystic, Connecticut is a wonderful little seaside town that feels like a must-do on a New England adventure. It is one of my favorite places in New England, and there is plenty to do here: history, culture, art, sailing. And, for seafood lovers, Mystic’s coastal location offers a variety of delicious seafood dining options

Like pretty much every other scenic New England town, there’s a cute little downtown area with great shopping, dining, and activities.

A few terrific things to do in Mystic:

Explore Mystic Seaport, a historic shipyard and museum destination you could spend hours touring
Watch the Mystic drawbridge (the Mystic River Bascule Bridge) go up, especially while enjoying some Mystic Drawbridge Ice Cream!
See the adorable beluga whales at Mystic Aquarium
Browse the epic shops in Olde Mystick Village including my personal favorite: Alice’s Haunted Little Bookshop

Hotel recommendation for Mystic: The Whaler’s Inn

Further reading on Mystic: Check out my tips for all the fun things to do, best restaurants to eat at, and the best places to stay in Mystic!

Day 6: Litchfield Hills, Connecticut

*Traveling in New England means sights like this!*

As you roadtrip New England, your next destination is the enchanting Litchfield Hills. This is another easy drive day, as the distance from Mystic to the Litchfield region is a short 2 hours. And if you’re traveling in the fall, the Connecticut fall foliage along this route creates a magical backdrop.

To me, this area in the northwest corner of the state is a hidden gem.

Here you’ll find all the classic New England pastimes you know and love. In particular, there is an abundance of outdoor activities (hiking, paddling, fishing) as well as exceptional antique shops.

The Litchfield Hills make up a large portion of this region, and include towns such as Torrington, Woodbury, Kent, Cornwall, and Washington (very English sounding names, aren’t they?)

A few excellent things to do in the Litchfield Hills:

Live out your Gilmore Girls Dreams. This region is well known for being the inspiration for the iconic tv show that perfectly encapsulates New England small town charm.
Grab ice cream from Arethusa Farm
Go covered bridge chasing – Bulls Bridge in Kent has a worthwhile nearby hiking trail
Hike to Campbell Falls, a beautiful waterfall (this trail technically takes you over the border into Massachusetts, too, so it’s a 2-for-1!)

Recommended hotel in the Litchfield Hills: The Mayflower Inn & Spa: legend has it that it was the inspiration for Lorelei Gilmore’s inn, the Dragonfly.

Day 7: Lenox, Massachusetts

*A fall New England road trip sure looks dreamy from this angle.*

Continue on your New England road trip into the Berkshires of Massachusetts. Here you will encounter art, nature, and culture combined. This region has been very popular among vacationers for many years. And the town of Lenox is the center of it all.

Best things to do in Lenox:

Enjoy a concert at the famous Tanglewood (these are a staple in summer, and you can hear everything from leading symphonies to folk singers like James Taylor
Take in a performance at Shakespeare & Company. This theatre produces excellent shows; I’ve been twice!
Take a hike on one of the area’s many scenic trails
Step back in time at the Ventfort Hall Mansion and Gilded Age Museum, a 1890s home that’s open for tours.
If you are interested in literature, you may also wish to stop by the Mount, Edith Wharton’s turn-of-the-century estate.

Where to stay in Lenox:

More resources for your trip to Lenox and the Berkshires:

🍁Best Restaurants in Lenox
🍁10 Charming Cabins in the Berkshires
🍁Best Hikes in the Berkshires

Day 8: Manchester, Vermont

A soldier's monument stands tall amidst the fiery red and orange leaves of autumn in the Northeast, with a clear blue sky above and a backdrop of a mountain. This image captures the vibrant fall colors, ideal for a Northeast road trip to see the season's change — *Vermont is all the classic New England vibes.*

Finally, you’ve made it into the spectacular state of Vermont (my personal favorite, if you couldn’t tell). It’s a fairly easy drive from the Berkshires in Massachusetts up to Manchester in the southwestern corner of Vermont, only a couple of hours. And this is another route that is especially glorious if you opt to do a New England fall road trip.

Manchester is one of the most beautiful places in Vermont, marrying quaint village charm with touches of modern luxury. It’s no surprise that it’s very popular among travelers.

Some of my favorite things to do in Manchester:

Tour Hildene, the beautiful Lincoln family home (Yes, some of Abraham Lincoln’s children lived here!)
Drive to the top of Mt. Equinox on Skyline Drive (or consider hiking the trail up to the summit)
In the fall, pick pumpkins from the patch at Equinox Valley Nursery (and don’t miss the cider donuts!)
Shop til you drop at Manchester’s many outlet stores
Dine at the stately Ye Olde Tavern
Pop into Northshire Bookstore, one of the leading independent bookstores in New England

Hotel Recommendation for Manchester: Kimpton Taconic Hotel

More resources on Manchester: Read my entire Manchester VT travel guide for more of the top Manchester activities, as well as these articles on the best restaurants, breakfast spots, and hotels in Manchester.

PS: If you’re very interested in exploring Vermont, a trip through Manchester, Burlington, and Stowe make the ideal Vermont road trip itinerary.

Day 9: Burlington, Vermont

an image of an empty shopping street on a sunny day. colorful banners cross over the blue sky and a long bricked walkway leads to a distant church - burlington vermont — *Burlington is a definite must visit on any tour of New England*

Just around 2 hours north of Manchester (taking the beautiful and scenic Route 7) you’ll find yourself in Burlington: Vermont’s biggest city. It’s also often mislabeled as Vermont’s capital, but that honor goes to Montpelier. Still, you’re likely to run into Bernie Sanders in either town!

Burlington is where my husband and I lived for several years. It’s a fantastic town that is hip, artsy, and full of good, local food. Seriously, in Vermont, you need to eat. There’s so much delicious cheese, coffee, beer, maple syrup, and much, much more.

To get you started on your culinary adventures, check out this post on my favorite Burlington breweries and bars , and this one on my beloved coffee shops. Oh, and don’t forget to enjoy brunch in BTV. We do breakfast here right.

The gem of Burlington is Lake Champlain, the sprawling, sparkling lake that the city overlooks. Here is the chance to go sailing, stand-up paddleboarding, or take a ferry across to New York state.

If you’d prefer to stay on dry land, visit one of the many beautiful parks and natural areas. Burlington is amazing for outdoor activities. If you want to get moving, the Burlington Bike Path stretches for miles, hugging the lake’s edge. This is ideal for running or cycling. You can even rent bikes right on the bike path.

More epic things to do in Burlington VT:

Sail on Lake Champlain on the Spirit of Ethan Allen cruise
Walk down Church Street for shopping, eats, people-watching, and more
Hike Mt. Philo, a nearby easy hike with the payoff of a fantastic view

Hotel recommendation in Burlington: Hotel Vermont

Even more resources for your Burlington trip:
🍁21 Hikes Near Burlington VT to Add to Your Bucket List
🍁10 Can’t-Miss Free Things to do in Burlington VT
🍁9 Incredible Day Trips from Burlington VT
🍁Where to Stay in Burlington VT in 2023: Best Burlington Hotels

PS: Considering visiting Burlington in 2024? It’s one of the cities that the total solar eclipse will pass fully over on April 8, 2024, so start planning ASAP!

Days 10 & 11: Stowe, Vermont

A vibrant 'Welcome to Stowe, Vermont' mural painted on the side of a classic blue New England building, complete with hanging flower baskets. This colorful greeting sets the tone for a picturesque stop on a road trip through New England. — *Stowe is about as picturesque a New England destination as can be.*

From Burlington, head south on I89 to Exit 10. From there, you’ll take the scenic Route 100 past Waterbury and out to Stowe. When people think of the classic Vermont places, they’re likely thinking of Stowe.

It’s absolutely gorgeous: a charming town surrounded by mountains. The short Main Street and its side streets boast a white-steepled church, an old-timey general store, and a ski museum.

Simply put, Stowe is adorable. I have been to Stowe countless times and I highly recommend it as one of the premier New England road trip destinations!

Wonderful things to do in Stowe:

Traverse the trails and property at the Trapp Family Lodge, and grab a beer afterwards at their European-style brewery and Bierhall
Shop the adorable shops on Main Street
Visit a haunted covered bridge if you dare (Emily’s Bridge)
Spend a day skiing on one of the area’s fantastic ski mountains
One of my number one tips: on your way to Stowe, stop by Cold Hollow Cider Mill for all things apple (a must-visit in the fall) and the Ben & Jerry’s Ice Cream Factory tour.

Where to stay in Stowe: Field Guide Lodge, Topnotch Resort, or the Trapp Family Lodge

More on Stowe: I have an entire post dedicated to Things to Do in Stowe, Vermont, the best restaurants, the best breakfast, the best hikes, the best hotels, everything!

Days 12 & 13: The White Mountains, New Hampshire

A serene lake reflects the vivid autumn foliage of New England, with a mix of green, yellow, and orange leaves against a clear blue sky. This peaceful setting is a highlight for travelers on a New England states road trip, offering a moment of reflection amidst nature's splendor. — *Any outdoor enthusiast is going to fall in love with this New Hampshire stop on their New England road trip!*

No adventure in New England could be complete without some mountain time. And this is especially true if you’re planning a New England fall road trip .

New Hampshire’s White Mountains are impressive and exciting. They’re the tallest in New England (with Mount Washington tallest of all) and offer spectacular hiking and more. There are several places you could base yourself during this portion of the road trip, but I recommend North Conway, Lincoln, or North Woodstock, as they each offer lots of amenities and accommodations, and are a reasonable distance from the most popular attractions in the region.

Unmissable things to do in the White Mountains:

Take in some of the coolest natural wonders of the White Mountains, such as the Basin, a granite “pothole” that is found at the base of a waterfall in Franconia Notch State Park
Go hiking! This is the #1 item on any New Hampshire bucket list. And here is a guide to some of the best hikes in New Hampshire.
Meander through Flume Gorge. This is a natural ravine that formed over many years and now a hiking trail with a boardwalk passes through it. This is a wonderful hike with some amazing scenery. Another spot that is extra special with the fall foliage
Clark’s Trading Post in Lincoln, an old-fashioned New Hampshire classic
A scenic drive along The Kancamangus Highway. This epic stretch of road runs 26 miles between Lincoln and Conway and is one of New Hampshire’s most scenic roads . There are many great spots to stop and explore further and this is undoubtedly one of the best places to see New England fall foliage.
Shop in North Conway, and don’t miss Zeb’s General Store for a taste of pure nostalgia.
Tube or paddle in the Saco River. On a friend’s recent bachelorette party trip, we used Saco River Tubing and had an absolute blast!
Near Bartlett you can stop by Diana’s Baths, a beautiful area of cascading waterfalls and gentle pools. On a hot summer’s day, it’s the perfect place to cool off.

Where to Stay in the White Mountains: Lumen Nature Retreat

More White Mountains travel guides:

🍁 Best Things to Do in North Conway, NH
🍁 Best Things to Do in Lincoln, NH
🍁 Best Things to Do in Franconia, NH
🍁 15 Amazing Cabins in the White Mountains, NH

Days 14 & 15: Portland, Maine

amy is wearing a bright orange sweatshirt and holding her toddler son in the air, both are smiling and there is a famous maine lighthouse beyond — *My son & I exploring Portland, Maine together*

Finally, the last state on the great New England road trip. This is Maine, “the way life should be.”

Maine is massive so there’s no way to do the state justice in this itinerary; I’m essentially covering a few of the must-see areas. You could spend weeks on a road trip of Maine alone. (See also these 8 autumn scenic drives in Maine delivering up insane fall colors).

If you do wish to explore the rest of Maine (and you absolutely should) I recommend taking a look at my epic list of 50+ Fun Things to Do in Maine, as well as this guide to the top places to visit in Maine.

But let’s continue with our amazing road trip!

Stop for a bit in Portland, a modern portside town that may surprise you. There’s a hip city right on the water in Portland, Maine, and this is a hot spot for restaurants, coffee shops, breweries, bakeries, and entertainment.

Fun things to do in Portland:

Visit a brewery. Beer lovers will be happy to know that Portland has 18 breweries all its own .
Check out one of several lighthouses in the area. There are 5 less than 20 minutes’ drive from Portland, including the iconic Portland Head Light.
Grab some of that famous Maine lobster.
Stuff your face with Maine potato donuts from local staple The Holy Donut
Walk the pretty Old Port and patronize the eclectic shops and restaurants
Don’t miss dining at Hot Suppa, a West End restaurant where I enjoyed the best breakfast of my life (and a spectacular maple latte)
Traveling with kids? The Children’s Museum of Maine on Thompson’s Point is a total blast!

Portland hotel recommendation: Hotel Francis in the West End

Further resources for discovering Portland:

🍁The Best Things to Do in Portland, Maine
🍁Weekend in Portland Itinerary
🍁7 Spots for the Best Breakfast in Portland Maine
🍁14 Exceptional Airbnb Portland Maine Rentals
🍁12 Best Hotels in Portland Maine

Days 16 & 17: Acadia National Park and Bar Harbor, Maine

A breathtaking aerial view from a cliffside, overlooking a tapestry of fall foliage in New England, with a backdrop of a calm bay meeting the Atlantic Ocean. This panoramic vista captures the essence of exploring New England, where land and sea meet amidst the splendor of autumn. — *Bar Harbor and Acadia are perfect stops on any road trip through New England.*

Now we travel north to Bar Harbor. Admittedly, it looks like a far drive on the map. In reality, from Portland to Bar Harbor is just over a 3-hour drive. And trust me, visiting Mt. Desert Island is SO worth it.

Bar Harbor is the seaside town that will be your base for exploring Acadia National Park. You will be in awe over this beautiful part of Maine. Here is where rocky cliffs tumble into the sea, with iconic lighthouses at the top.

There’s abundant wildlife on land and in the sea, and countless opportunities for terrific hiking.

But the region is not just about the outdoors. Bar Harbor has lovely shops, restaurants, and extremely cozy inns. Truly, the region is ideal for travelers of all kinds. You’ll also find great camping, cabins, and vacation rentals in and near Acadia, too.

My top recommendations in Acadia National Park and Bar Harbor:

Tackle the exhilarating Beehive Hike, that involves a bit of climbing and rewards you with unparalleled views
Order popovers at the Jordan Pond House (delicious!)
Take a whale watch or other wildlife tour from Bar Harbor
Drive up Cadillac Mountain before dawn to catch the sunrise from the first place light touches in the Continental US
Marvel at the natural wonder of Thunder Hole
Bike the Carriage Roads in Acadia National Park

Bar Harbor hotel recommendation: The Bar Harbor Inn

More on Acadia: Check out my 3 Day Bar Harbor and Acadia National Park Itinerary for an awesome trip!

Day 18: Portsmouth, New Hampshire

A charming street in a New England town during a getaway, featuring historic brick buildings with a quaint coffee shop, and the steeple of a white church rising against a sky with puffy clouds. The inviting atmosphere is perfect for a leisurely stroll and exploration. — *Visiting the Seacoast is an essential part of any coastal New England road trip*

Your New England driving tour itinerary is nearing its end, but you’ve got a few more stops to make—-stops you won’t want to miss.

Portsmouth is first. We’re back in New Hampshire now! Between Maine and Massachusetts, New Hampshire is home to a very small strip of coastline. The hub of the Seacoast is Portsmouth, a small yet lively city with a great deal of history. You can see colonial architecture all over this beautiful city.

Taking a New England winter road trip? Portsmouth should definitely be on your list, as they do a month of celebrations and events with Vintage Christmas, one of the most magical New England Christmas celebrations !

Best things to do in Portsmouth:

Strawbery Banke Museum: an outdoor living history museum.
Dine at one of the many awesome restaurants: Portsmouth has become a major foodie destination in recent years
Go shopping at the numerous boutiques around town. Some standouts: Gus & Ruby Letterpress, Pickwick’s Mercantile, and G. Williker’s Toy Shop
Be surrounded by books and grab a tasty beverage at Book & Bar
Wander the lovely Prescott Park
Attend some award-winning theatre at Seacoast Repertory Theatre

Hotel suggestion in Portsmouth: The Hotel Portsmouth

Further Portsmouth NH travel resources for your trip:
🍁The Best Things to Do in Portsmouth, NH
🍁Top 10 Bars in Portsmouth NH

Day 19: Salem, Massachusetts

A historic dark wood-paneled house in New England, decorated with autumnal pumpkins and hay bales, captures the seasonal charm on a driving tour. The bright fall foliage provides a colorful contrast to the classic architecture, inviting visitors to explore the region's heritage

Your final stop is the historically infamous Salem, Massachusetts. And though you’ll definitely want to spend time exploring its history with the Salem Witch Trials, there’s plenty to do in the area that isn’t witchy, too.

You can hit the highlights of Salem in one day, or extend for another 2-3.

If possible, you don’t necessarily want to plan your trip to Salem to coincide with Halloween. Although the town has a distinct, fun vibe this time of year, October is also its busiest and most crowded month.

No matter when you go, however, there are definitely some things not to be missed:

Go to The Witch House, an atmospheric home you’ve definitely seen on Instagram, and a building that is one of the only Salem locations with direct ties to the witch trials. (One of the judges lived here).
Get witchy in the magickal shops. Whether you want something more fun and touristy, or you’re after the real deal, Salem has a wide range of shops selling all kinds of goods.
Tour the House of the Seven Gables
Walk the neighborhoods around Federal Street and admire the stately historic homes
Find the Hocus Pocus film locations! (Use my guide to take a DIY Hocus Pocus tour)
Get spooked on a nighttime ghost tour (top recommendations here!)
Grab a photo with Samantha at the Bewitched Statue

Hotel recommendation for Salem: The Hawthorne Hotel or Hotel Salem (they have a great rooftop bar)

More on Salem: Check out its great restaurants, scope out some of its haunted history, and maybe even stay overnight in one of Salem’s classic New England inns or Airbnbs!

Nearby towns of Rockport, Gloucester , and Marblehead are worth visiting too if you’d like to explore more of this area of coastal New England.

Day 20 / End: – Boston, Massachusetts

You did it! You’ve completed an epic New England road trip! Congratulations! You’ve seen some of the prettiest places in the country, and you did it all by car!

Days 21+: Optional Add-Ons: Cape Cod/Nantucket/Martha’s Vineyard

A classic New England lighthouse with a white facade and adjoining keeper's house, set against a clear blue sky. A well-tended lawn with a concrete pathway leads to the building, symbolizing the maritime heritage encountered while traveling through New England

You may be wondering why I didn’t include some of New England’s coastal gems on this New England road trip itinerary? I did this because destinations such as Cape Cod, Nantucket, and Martha’s Vineyard are harder to get to and don’t fit in well with the traditional road trip format. After all, Nantucket and Martha’s Vineyard are islands, so they are not an easy destination to access without in-depth planning.

Not only are they more complicated to travel to, these Massachusetts coastal destinations are terrific and truly worthy of their own vacations. I highly recommend devoting a trip specifically to exploring New England’s amazing coast.

If you wish to add to your road trip, by all means, hop in the car and continue the drive to Cape Cod. From there you can easily take a day trip to Martha’s Vineyard or Nantucket. And I hope these resources will help you as you plan:

More travel ideas here:

The Ultimate New England Road Trip Map (2-3 weeks)

The map below includes all of the destinations I’ve outlined above.

In need of some extra New England road trip ideas? If you’re limited on time, check out my Northern and Southern New England road trip itineraries. These are ideal for 5 day, 7 day, or 10 day New England road trips. Your own personal planning maps are below!

Northern New England Road Trip 7-10 Day Itinerary

Boston, MA
Woodstock, VT
Waitsfield, VT
Stowe, VT
Lincoln, NH
Portland, ME

Here’s a great New England road trip route if you just don’t have time to go everywhere, but you want to see the highlights of northern New England. In any trip you’ll have to make some choices about what to see and what to miss, sadly, but with this road trip itinerary, you’ll definitely have a broad experience of Northern New England.

This one week New England itinerary contains many of the same stops you’ll find on the ultimate version (that covers all six states). But this one also has the addition of Woodstock, Vermont, which is a classic New England spot, really a ‘Currier and Ives town.’

Southern New England Road Trip 7-10 Day Itinerary

Boston, MA
Provincetown, MA
Newport, RI
Providence, RI
Stonington, CT
Litchfield Hills, CT
Lenox, MA
Gloucester, MA
Salem, MA

The Southern New England road trip route is ideal for those who really seek a coastal trip, or who aren’t quite as interested in exploring the mountains. This trip adds a whole bunch of extra stops so you can really dive into coastal New England.

It gives you a feel for the more outdoorsy areas of these southern New England states, too, as the itinerary brings you through the Berkshires, and through charming parts of Connecticut. Definitely an option for a lovely New England summer road trip itinerary.

Shorter Scenic Drives in New England

Are you just looking for a short scenic route that allows you to see dramatic coastal cliffs, mountainscapes, scenic countryside, and more of New England’s charm?

Whether you’re looking for fall scenic drives in New England, beautiful routes along the coast, or just a short yet pretty New England drive, you might just find what you’re looking for on this list of short, scenic drives in New England.

Scenic Drives in New Hampshire

A scenic road in New Hampshire with a covered bridge and fall foliage — *This was even prettier in person.*

The Coastal Byway (Route 1A)

Location: Portsmouth to Seabrook

Distance: 18.5 miles

Where to Stop:

Robert Frost Scenic Byway

Location: Southern New Hampshire

Distance: 43 miles (The Old Stagecoach Byway and the Robert Frost Byway combined)

Where to Stop:

Robert Frost Farm State Park, Derry
Civil War Memorial, Chester
Matthew Thornton House, Derry
Town Beach, Hampstead

New Hampshire Route 112 (Kancamagus Highway)

Location: Conway to Bath

Distance: 56.39 miles

Where to Stop:

Sabbaday Falls
Albany Covered Bridge
Swift River Lower Falls
Russell-Colbath House
Sugar Hill Scenic Overlook

The Lake Winnipesaukee Loop

Location: The Lakes Region

Distance: 97 miles

Where to Stop:

George’s Diner, Meredith
Mt. Major Trail, Alton
Dewey’s Ice Cream Parlor and Cafe, Center Harbor
Cotton Valley Rail Trail, Wolfeboro
Abenakee Tower, Tuftonboro

Scenic Drives in Maine

Moosehead Lake

Location: Kennebec and Moose River Valley

Distance: 59 miles

Where to Stop:

U.S. Coastal Route 1

Location: Kennebunkport to Bar Harbor

Distance: 200 miles

Where to Stop:

Goose Rocks Beach, Kennebunkport
Portland Head Light, Cape Elizabeth
Old Orchard Beach Boardwalk, Old Orchard Beach
The Holy Donut, Portland
Farnsworth Art Museum, Rockland
Jordan’s Restaurant, Bar Harbor

Acadia All American Road from Trenton to Acadia

Location: Trenton to Bar Harbor

Distance: 40 miles

Where to Stop:

Jordan’s Restaurant, Bar Harbor
Sand Beach
Thunder Hole
Bar Harbor Inn & Spa

Scenic Drives in Vermont

A close up of the South Vermont 100 sign on a scenic byway in Vermont — *So many quaint towns to see on Route 100!*

Route 100

Location: Wilmington to Jay

Distance: 184 miles

Where to Stop:

Molly Stark State Park, Wilmington
Dot’s Restaurant, Wilmington
The Vermont Country Store, Weston
Green Mountain Sugar House, Ludlow
Moss Glen Falls, Granville
Ben & Jerry’s Factory, Waterbury
Cold Hollow Cider Mill, Waterbury Center
Trapp Family Lodge, Stowe

Route 9 – The Molly Stark Byway

Location: Brattleboro to Bennington

Distance: 40.1 miles

Where to Stop:

Vermont Country Deli, Brattleboro
Creamery Bridge, Brattleboro
Southern Vermont Natural History Museum, West Marlboro
Dot’s Restaurant, Wilmington
Hogback Mountain Scenic Lookout, Wilmington
Bennington Battle Monument, Bennington
The Apple Barn and Country Bakeshop – Bennington

Route 7

Location: Bennington to Burlington

Distance: 122 miles

Where to Stop:

The Bennington Battle Monument, Bennington
The Robert Frost Stone House Museum, Shaftsbury
Cider donuts at the Equinox Valley Nursery, Manchester
Downtown Murals, Rutland
Woodchuck Cider, Middlebury
The Burlington Waterfront – Burlington
Church Street/Downtown – Burlington

Rhode Island Scenic Drives

Ocean Drive

Location: Fort Adams Park to Bellevue Ave

Distance: 10 Miles

Where to Stop:

Castle Hill Lighthouse
Brenton Point State Park
Fort Adams Park
The Breakers
Marble House
Rough Point
The Elms
The Red Parrot Restaurant

Scenic Drives in Connecticut

Connecticut State Route 169

Location: Norwich to Woodstock

Distance: 36 miles

Where to Stop:

Lisbon Meadows Park, Lisbon
Prudence Crandall Museum, Waterbury
New England Center of Contemporary Art, Brooklyn
Roseland Cottage, Woodstock

Connecticut Shoreline Drive

Location: New Haven to Stonington Borough

Distance: about 80 miles (depending on which routes you take!)

Where to Stop:

Eat in Little Italy, New Haven
Hammonasset Beach State Park, Madison
Harvey’s Beach, Old Saybrook
Rocky Neck State Park, East Lyme
Mystic Aquarium, Mystic

Scenic Drives in Massachusetts

The Berkshires

Location: Stockbridge to Williamstown

Distance: 35 miles

Where to Stop:

Norman Rockwell Museum, Stockbridge
Berkshire Botanical Garden, Stockbridge
The Mount, Edith Wharton House, Lenox
Berkshire Museum, Pittsfield
Hancock Shaker Village, Hancock
Mount Greylock , North Adams
Massachusetts Museum of Contemporary Art, North Adams
Williams College – Williamstown

Essex Coastal Scenic Byway

Location: Gloucester to Newburyport

Distance: 24 miles

Where to Stop:

Hammond Castle Museum, Gloucester
Crane Wildlife Refuge, Essex
Eat at the Clam Box, Ipswich MA
Plum Island Beach, Newburyport
Maudslay State Park, Newburyport

Wrapping Up this Northeast Road Trip

I hope this New England travel guide has given you all the information you need to help you plan a trip to the region’s most exciting and gorgeous places. With multi-day options to choose from and choices that are great for every season, I have aimed to cover all of the top places to road trip throughout these six amazing states.

Even more resources for your New England adventures:

🍁25 Fantastic New England Day Trips
🍁Hidden Gems in New England: 15 Secret Places to Visit
🍁Best Fall Foliage New England Tours Worth Your Money

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