A Spectacular Show of Color on this 2-Week Autumn Road Trip Through New England: A Leaf-Peeping Odyssey

A Spectacular Show of Color on this 2-Week Autumn Road Trip Through New England: A Leaf-Peeping Odyssey

Embarking on a road trip through New England during the peak of autumn is like stepping into a vivid painting of fiery reds, oranges, and golds.

Over the course of two weeks, you can experience the spectacular show of colors, quaint towns with charming boutiques and world-renowned restaurants, along with breathtaking sightseeing spots.

This itinerary will guide you through the best places to visit, ensuring you don't miss a single leaf-peeping moment.

Pen Pal Adventure Book 


Week 1: Exploring Massachusetts and Vermont

Day 1: Boston, Massachusetts - START HERE

  • Start your journey in the historic city of Boston. Visit the Freedom Trail, Boston Common, and Quincy Market for a taste of the city's rich history.

Day 2: Northampton, Massachusetts (100 miles)

  • Head west to Northampton, known for its vibrant arts scene and eclectic boutiques. Stroll along Main Street and explore local art galleries.

Day 3-4: The Berkshires, Massachusetts (50 miles)

  • Drive to the Berkshires, a haven for leaf peepers. Take a scenic drive along Route 7 and visit the Norman Rockwell Museum and The Clark Art Institute.

Day 5: Woodstock, Vermont (150 miles)

  • Cross into Vermont and arrive in Woodstock, a quintessential New England town. Explore the historic village green and browse the local shops.

Day 6-7: Stowe, Vermont (45 miles)

  • Drive to Stowe, known for its stunning fall foliage. Hike the Stowe Pinnacle Trail for panoramic views and enjoy the charming town.

Big Leaf 


Week 2: New Hampshire and Maine Adventures

Day 8: White Mountains, New Hampshire (75 miles)

  • Enter the White Mountains region and experience breathtaking vistas on the Kancamagus Highway. Don't miss the Flume Gorge.

Day 9: North Conway, New Hampshire (40 miles)

  • Drive to North Conway, a haven for outdoor enthusiasts. Explore the outlet shops and embark on a scenic train ride.

Day 10: Portland, Maine (70 miles)

  • Head to Portland, a vibrant coastal city. Stroll along the Old Port waterfront, visit boutique shops, and savor fresh seafood.

Day 11-12: Bar Harbor and Acadia National Park, Maine (170 miles)

  • Drive to Bar Harbor and Acadia National Park. Hike Cadillac Mountain for sunrise and explore the town's charming shops and restaurants.

Day 13-14: Kennebunkport, Maine (170 miles)

  • Head south to Kennebunkport, a picturesque coastal town. Visit Dock Square for boutique shopping and dine at a local seafood restaurant.

Lincoln, NH 

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