New York to Boston: A New England Road Trip

This New England adventure blends big-city energy, charming small towns, and spectacular autumn scenery into one unforgettable road trip. Starting with three nights in vibrant Lower Manhattan, you’ll have time to enjoy New York’s iconic sights before collecting your car and heading north into the heart of New England. Each stop brings its own charm—from riverside tranquillity in Woodstock to the cosy mountain vibes of Stowe and North Conway, followed by the foodie culture and coastal character of Portland’s Old Port. As you continue toward Boston, you’ll experience classic New England landscapes, scenic byways, and picture-perfect fall foliage. Finishing with a stylish stay in Boston, this itinerary combines varied hotels, stress-free driving, and a perfect mix of city exploration, nature, and relaxation. It’s the ideal way to enjoy the best of the U.S. Northeast in one beautifully paced trip.