Boston & New England — 9-Day Self-Guided Motorcycle Tour
Ride a 1,190-mile self-guided motorcycle adventure through Massachusetts, Vermont, New Hampshire, and Maine, combining some of New England’s best mountain roads, coastal scenery, historic towns, and classic motorcycle routes.
Your journey begins in Boston, where you can explore the city before picking up your motorcycle in Woburn and heading west into Vermont. The first riding day follows the Molly Stark Scenic Byway into the Green Mountains, tracing a historic route connected to the Battle of Bennington before ending in Wilmington.
From Wilmington, ride north on Vermont Route 100, one of the most scenic roads in New England. The route winds through mountain valleys, historic villages, and classic Vermont countryside, with a stop at Plymouth Notch, birthplace of President Calvin Coolidge, before reaching Newport near Lake Memphremagog.
Continue into New Hampshire and tackle the legendary Kancamagus Highway, riding through the White Mountain National Forest past mountain passes, covered bridges, waterfalls, and swimming holes. The day ends in Portland, Maine, known for its waterfront, seafood, and vibrant food scene.
From Portland, follow Maine’s dramatic coastline north toward Bar Harbor and Acadia National Park. Expect coves, fishing villages, lobster boats, and winding coastal roads before reaching one of the Northeast’s most beautiful national parks. Cadillac Mountain, rocky shoreline, and Atlantic views make this one of the highlights of the trip.
The next leg explores more of Maine’s rugged Atlantic coast on the way to Bangor, with lighthouses, wild blueberry country, osprey, eagles, and traditional New England seaside villages along the route. From Bangor, head south on Old Route 1 to Portsmouth, New Hampshire, a historic coastal city filled with seafood, breweries, and centuries-old architecture.
The final ride follows the coast back toward Boston. Take your time through Rockport, Gloucester, Essex, and Salem, with the option to stop at Woodman’s of Essex, birthplace of the fried clam, before returning to the Boston area.
The trip covers 9 days and 1,190 miles, with riding days ranging from 79 to 231 miles. Expect summer temperatures around 50–80°F, cooler mountain and coastal conditions, occasional rain, and limited cell coverage in rural Vermont and Maine.
This is a self-guided tour, with no fixed departure times—ride at your own pace and explore along the way. Booking the Experience includes a detailed tour booklet with the complete itinerary, daily routes, mileage, recommended stops, restaurants, lodging suggestions, rider tips, and Google Maps navigation links.
9 Days · 1,190 Miles · Boston, Vermont, New Hampshire & Maine · Self-Guided
