There’s something timeless and cinematic about New England. Think winding roads framed by golden leaves, coastal towns with lighthouses and lobster rolls and villages where time slows just enough for you to breathe deeper. Whether you’re chasing fall foliage, craving a cozy weekend getaway or just need a change of pace, a New England road trip delivers.
With six unique states to explore — Connecticut, Rhode Island, Massachusetts, Vermont, New Hampshire and Maine —you can mix mountains with coastlines, historic charm with modern luxury and solitude with small-town magic. It’s the kind of trip where you create your own rhythm: detour for apple cider donuts, pull over for a view, get lost in antique shops and arrive somewhere even better than planned.
Here’s how to plan the ultimate New England road trip, whether you’ve got three days or a full week to roam.
How Many Days Do You Need For A New England Road Trip?
The sweet spot for a New England road trip is seven to 10 days if you want to hit multiple states and soak in a variety of landscapes. But even a three to four day trip can be incredible if you focus on one region—like coastal Maine or western Massachusetts. You’ll want enough time to enjoy some moments of spontaneity like a roadside maple syrup stand, a scenic overlook you didn’t expect or a small museum that pulls you in. A full week allows you to explore at a more relaxed pace, without feeling like you’re rushing from state to state. Travelers would be wise to avoid trying to conquer all of New England in one go. You’ll miss what makes it special.
Fall is the most popular time to go to New England, especially from late September to late October, but summer and spring are beautiful too. Winter has its charm if you’re into snow-dusted villages and cozy inns. Overall, when visiting, think quality over quantity. You don’t need to rush through all six states. Focus on a few that speak to your vibe.
What Is The Most Scenic Drive In New England?
You can’t go wrong with coastal Route 1 or Vermont’s Route 100, but if you’re only picking one, the Kancamagus Highway in New Hampshire is legendary. Known as “The Kanc,” this 34.5-mile stretch cuts through the White Mountains and delivers show-stopping fall foliage, hiking trailheads and river views. There are no billboards and no gas stations to interrupt the views or ruin the experience surrounded by nature. There are just trees, air and elevation.
Where To Stop On A New England Road Trip
Each state has its own rhythm, so build your route based on your pace. There are so many options for travelers to explore throughout this popular road trip destination. And what travelers stop and see depends on their personal preferences and how much time they have to explore. So it is possible to take multiple trips to explore New England and see completely different things. But there are a few places that have become staples for the classic New England road trip. Here are must-visit stops across the region:
Portsmouth, New Hampshire
An underrated coastal gem, Portsmouth blends maritime history with indie energy. Think cobblestone streets, waterfront walks, and cozy cafes. And travelers can stroll through the Strawbery Banke Museum, grab oysters at Row 34, or take a harbor cruise. It’s polished, but unpretentious.
Plus, the city’s Prescott Park often hosts outdoor concerts and theater performances during the warmer months. That means that visitors can enjoy the more easy going and communal vibes that New Hampshire has to offer on the waterfront, with some much anticipated entertainment. In Market Square there are many boutique shops that have everything from handcrafted goods to indie bookstores. Even in the winter, the town is relatively walkable and the festive lights bring the area to life.
Portland, Maine
Hip, artsy, and full of flavor, Portland is one of New England’s coolest small cities. The Old Port is lined with boutiques and breweries, while nearby Peaks Island makes for a peaceful afternoon trip. Don’t leave without grabbing a lobster roll from Eventide Oyster Co. or checking out a local gallery. Thanks to its blend of innovative chefs and longstanding coastal traditions, Portland’s food scene has consistently ranked among the best in the U.S, so foodies have plenty to enjoy. You’ll also find Black-owned bookstores, coffee shops, and a local community that’s pushing culture forward.
For a cultural tour of the area, try visiting The Portland Museum of Art, which anchors the downtown art district. Many regional creators are showcased, which might be the perfect way to check out the creative scene in Portland. In the evening, the city’s music venues give travelers plenty of ways to end the night, whether intimate jazz lounges or indie stages are more your style.
Bar Harbor & Acadia National Park, Maine
This is where mountains meet the sea. Acadia National Park offers jaw-dropping views, sunrise hikes on Cadillac Mountain, and scenic drives like Park Loop Road. The nearby town of Bar Harbor is all charm—ice cream, seafood, and small-town joy. Rent bikes, picnic on the rocks, or book a lobster boat tour to connect with the local working-class history of the coast.
Wildlife enthusiasts can spot all types of creatures throughout the park’s diverse ecosystems. Then, Bar Harbor’s Shore Path is an easy and scenic walk that has picture perfect views without all the strenuous hiking. During peak season, there are ranger led talks and stargazing opportunities, so this destination has drawn attention from people all over.
Woodstock, Vermont
Straight out of a postcard, Woodstock delivers covered bridges, antique shops, and one of the best downtown strolls in the region. Visit Billings Farm & Museum, grab local cheese, and stay at a classic New England inn. The pace is slow, and the hospitality feels personal. Come fall, the color of the trees turn to a photogenic fire red.
The nearby Marsh-Billings-Rockefeller National Historical Park offers some easy trails through scenic forests. But Woodstock’s farmers market and weekend craft fairs give travelers a taste of the region’s popular farm to table culture. In the winter the area is cozy and is complete with horse drawn sleigh rides. Visitors can also check out the small galleries and artisan studios around town which highlight Vermont’s long standing creative traditions.
Stowe, Vermont
Known for skiing in the winter and foliage in the fall, Stowe is a vibe. Hike the Stowe Pinnacle Trail, ride the Gondola SkyRide, and enjoy the local food scene. Stop by Cold Hollow Cider Mill for cider donuts and a taste of autumn. It’s a place where cozy meets wild, and both feel welcome.
This town is home to the Trapp Family Lodge, which was founded by the real life family behind “The Sound of Music.” This unique site adds an intriguing cultural layer to the region. In the summer, mountain biking and waterfall hikes are popular around Smugglers Notch. Alternatively, travelers can check out breweries like The Alchemist which is known for its acclaimed Heady Topper IPA.
The Berkshires, Massachusetts
A haven for artists, writers, and romantics, the Berkshires blend mountain scenery with cultural richness. Catch a performance at Tanglewood, visit Mass MoCA, and soak in the peaceful surroundings. Towns like Lenox and Great Barrington offer boutique shopping and spa-worthy stays. The Berkshires are also deeply rooted in Black American history. Check out The W.E.B. Du Bois Homesite in Great Barrington for a culturally rich experience.
The region has one of the best farm to table dining scenes in New England, with chefs sourcing ingredients from the local hills and valleys. Outdoor enthusiasts can enjoy miles of hiking trails, including some sections of the Appalachian Trail that cut through the area. Even small towns have unique museums, music venues and artisan makers.
Newport, Rhode Island
If your road trip needs a luxe coastal detour, Newport delivers. Tour the Gilded Age mansions, walk the Cliff Walk, and catch sunset at Castle Hill Inn. It’s old-money meets sea breeze, and a reminder that New England does elegance with ease. There’s also a lively Black arts community here that’s starting to gain more recognition, adding texture beyond the tourist facade.
Newport’s sailing culture is legendary since it has hosted America’s Cup races for decades, so it is a bucket list stop for many maritime fans. For curious visitors, downtown is packed with seafood shacks, independent shops and harbor side patios, which come alive in the summer. Events like the renowned Newport Jazz Festival and Newport Folk Festival bring global audiences to the waterfront each year, so road tripping travelers can plan their visit with this in mind.
Frequently Asked Questions
What is the best month to go to New England?
October is peak leaf-peeping season, especially during the first two weeks. For fewer crowds and great weather, late September or early June are also excellent choices. Summer (July–August) brings festivals and coastal energy, while winter is best for ski towns and holiday markets.
Which New England state is the prettiest?
It depends on your taste. Vermont is beloved for its rolling hills and fall foliage, while Maine offers rugged coastline and iconic lighthouses. Massachusetts gives you everything from art towns to beaches. If you’re chasing nature and quiet, Vermont. If you want seafood and sea views, Maine.
What is the best New England state to visit in the fall?
Vermont takes the crown for fall. The color palette, the pace and the cider mills is most iconic. However, don’t sleep on New Hampshire’s Kancamagus Highway or the Berkshires in Massachusetts. All give you peak foliage with different vibes.
