Buckle up — this isn't your typical road trip. Hike, shop, dine, and sail your way through New England with a custom itinerary from our partner, All Roads North. Immerse yourself in Maine's seafaring history while hauling traps on a lobster boat, drive up Mount Washington on the famed 7.6-mile Auto Road, detour in Vermont to meet and work alongside local cheese and maple syrup producers, and more. Travel south on Route 100 following the Mad River Valley through the Southern Green Mountains to the far western edge of Massachusetts. You’ll get your culture fix in the Berkshires, home to acclaimed institutions including Tanglewood, the Clark Institute and Mass MOCA. Stay in hotels and inns delivering five-star New England hospitality along the way.