The Perfect New England Autumn Road Trip in 10 Days

New England is an iconic fall destination for so many reasons. There is a nip in the air, and the majestic forests are ablaze with vibrant colors. This is the ideal season for strolls, hikes, and adventure. The New England Region is home to five of the ten smallest states in the United States, making it the perfect region for a road trip. Follow this ultimate fall road trip itinerary for an unforgettable ten days surrounded by the magic of autumn.



This journey is a southwest-to-northeast route, beginning in Connecticut and winding along the coast on Route 95 to Rhode Island before turning north to Boston and Western Massachusetts. Continuing North from the Bay State, this road trip snakes through the hills and valleys of Vermont and New Hampshire before returning to the coast and proceeding to Maine. Although this is the final stop on our itinerary, travelers can relish this autumn road trip through all the memories to be made along the way.

10 Day 1: Johnson’s Glass House And New Haven Style Pizza in Connecticut

Day one of the itinerary is dedicated to picking up the rental car in Hartford or packing one’s own vehicle for the trip. Camping and hiking gear are recommended for travelers wishing to immerse themselves in the outdoors along the route, as there are many opportunities to do so. As these activities won’t occupy the whole day, travelers should begin with the stunning views at The Glass House, designed by renowned architect Philip Johnson. Drive to New Haven for the first overnight, and try New Haven-style pizza at Frank Pepe Pizzeria Napoletana, which opened in 1925.


9 Day 2: Cliff Walking And Craft Beer In Rhode Island

On the second day, make the short drive to Rhode Island, the smallest state in the US Travelers head to the Block Island Ferry to board a cruise to beautiful Block Island for a stroll amongst the fall foliage while enjoying views of the nearby sound and the Atlantic Ocean. After the return ferry voyage, it’s a short ride to the trailhead of the Newport Cliff Walk. This scenic walk runs along the city’s rocky coastline and includes paved sections ideal for beginners and rocky areas for advanced hikers. Wind down the day with a tour at one of Providence’s many craft breweries.

Related: Small State Tourism: Top TripAdvisor Attractions In Rhode Island

8 Day 3: Urban Adventure In Boston and Cambridge

On the third day, travelers cross into Massachusetts and make a stop in Boston. Take a tour of old Boston, and enjoy the fall foliage against the historical backdrop of Boston Common. It’s only a short ride on the metro system to Harvard Square, in the neighboring city of Cambridge. Explore the courtyards, museums, and timeless beauty of Harvard University, the oldest college in America. The fall foliage along the Charles River is well worth a stroll at sunset. Travelers should enjoy a relaxing stay in Boston overnight and rest well for a scenic drive through Massachusetts the next morning.


7 Day 4: The Berkshires, Bash Bish Falls, And The Mohawk Trail In Massachusetts

This day is fully dedicated to taking in fall foliage by car and on foot. Get an early start to drive two hours west on Highway 90 to The Berkshires, a region of hills and charming small towns. Visitors can stretch their legs at the River Walk in central Great Barrington. It’s well worth making a small detour to stop at Bash Bish Falls, a serene waterfall with a tragic history. For hiking and camping, continue south to Mount Washington State Forest or drive north to the Mohawk Trail. A scenic byway that dates back to its early days as a trading route established after the last ice age, the Mohawk Trail is ablaze with autumnal splendor in the autumn.

Related: 5-Day Bucket-List Road Trip Circuit : Explore Massachusetts

6 Day 5: Scenic Drives, Sugar Houses, And A Stay In A Log Cabin In Vermont

Travelers take the Mount Equinox Skyline Drive from Massachusetts into Vermont and all the way to the top of Mount Equinox for amazing views. Merge onto Route 7 and continue north through Green Mountain State Forest and its miles of breathtaking woods. To sample an authentic flavor of Vermont, visitors can visit one of the quaint Sugar Houses that make Maple Syrup, for which the state is famous. After a long day behind the wheel, travelers can relax in a traditional log cabin or tiny house.


5 Day 6: Historical Burlington, Vermont, And Lake Memphremagog

This leg of the itinerary begins with a four-hour drive north to Burlington, Vermont. Here, travelers should restock any necessary supplies. Visitors shouldn’t miss a historical Burlington tour to learn about its long and colorful history. The itinerary then leads through the city of Newport, where visitors take a cruise on Lake Memphremagog, a 27-mile-long lake straddling the US and Canadian borders and embraced by blazing fall foliage in the autumn.

4 Day 7: Scenic Train Journeys And Hiking In New Hampshire’s White Mountain National Forest

The first stop in New Hampshire is a little unusual for a road trip: a train journey! The Conway Scenic Rail Journey offers roundtrip schedules from one hour to 5.5 hours. Passengers comfortably take in sprawling views of the Mount Washington Valley in multicolor glory from the vintage railway cars. Explore the mountains more intimately with a hike in the White Mountain National Forest. Hikers can choose from a selection of campgrounds and cozy cabins in the area to make themselves at home in nature.

3 Day 8: Bar Harbor And Hiking On Mount Desert Island

On this day, road trippers will cross into Maine following coastal Highway 1. Driving along the state’s southern edge is the perfect opportunity to view fall foliage against the expansive background of the Atlantic Ocean. After the lengthy scenic drive, a rest day in Bar Harbor on Mount Desert Island is in order. There are hiking trails of all skill levels on the island. It is a great place to recharge and prepare for the next leg of the road trip.

Related: 5-Day Bucket-List Road Trip Circuit: Explore Scenic Maine

The itinerary calls for a day full of adventures in 100-year-old Acadia National Park. Take the Jordan Cliffs Loop hike for an advanced, challenging hike with sweeping views. Alternatively, Jordan Pond Path offers a medium-intensity hike overlooking the Pond’s crisp, blue waters. Travelers not interested in hiking can still enjoy nature on a fall foliage drive along Park Loop Road. But perhaps the easiest way to enjoy this scenic stretch of road is to take the seasonal shuttle. As evening falls, hikers can camp in the park at designated campsites.


1 Day 10: Try Local New England Cuisine And Canoe In Downeast Lakes Community Forest

The final day of the road trip begins with a restful morning of canoeing at Downeast Lakes Community Forest. In the afternoon, travelers should complete the two-hour drive to Bangor, Maine, to enjoy quintessentially New England cuisine like lobster rolls, fresh blueberries, Indian pudding, and clam chowder. Follow lunch with a stroll through the leafy Rolland F. Perry City Forest. Known locally as City Forest, the 680-acre preserve includes wildlife habitat and an array of outdoor activities in all seasons. Travelers finish the road trip here in Bangor, then return the rental car and head to Bangor International Airport to depart for the next destination.

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