7 Day New England Road Trip Itinerary

7 Day New England Road Trip Itinerary

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Prepared by: [YOUR NAME]

Travel Dates : [DATE]

Get ready for an amazing adventure through New England with our 7-day road trip itinerary. From historic Boston to the stunning landscapes of Maine and Vermont, we've mapped out the best spots for you to explore. With top-rated restaurants and must-do experiences along the way, get set to make unforgettable memories on this epic journey through New England.

Day 1: Arrival in Boston, Massachusetts

  • Morning: Begin your New England adventure by exploring the historic Freedom Trail, which winds through Boston's iconic landmarks such as Faneuil Hall and the Paul Revere House. Learn about the city's rich history and revolutionary past.

  • Afternoon: Immerse yourself in the maritime history of Boston at the Boston Tea Party Ships & Museum. Then, take a leisurely stroll through Boston Common, the oldest public park in the United States, and enjoy the serene greenery amidst the bustling city.

  • Evening: Treat yourself to a delectable seafood dinner at Legal Sea Foods or Neptune Oyster, where you can savor fresh catches of the day and signature dishes amidst a lively atmosphere.

Day 2: Boston to Portland, Maine

  • Morning: Depart from Boston and head north towards Portland, Maine. Along the way, make a stop in Salem, Massachusetts, to visit the Witch Trials Memorial and learn about the infamous events of 1692.

  • Afternoon: Arrive in Portland and explore the vibrant Old Port district, known for its charming cobblestone streets, boutique shops, and bustling waterfront. Take in the picturesque views of Casco Bay and browse through local artisanal crafts.

  • Evening: Indulge in the quintessential Maine dining experience with a fresh lobster dinner at Eventide Oyster Co. or Street & Co., where you can enjoy expertly prepared seafood dishes in a cozy coastal setting.

Day 3: Portland to Acadia National Park

  • Morning: Depart from Portland and embark on a scenic drive to Acadia National Park, stopping along the way to admire iconic lighthouses dotted along Maine's rugged coastline, including the picturesque Portland Head Light.

  • Afternoon: Arrive at Acadia National Park and spend the day exploring its breathtaking landscapes, from granite peaks to rocky shorelines. Choose from a variety of hiking trails, scenic drives, or leisurely walks along the coastline.

  • Evening: Relax and unwind with a delightful dinner at Jordan Pond House, overlooking the serene waters of Jordan Pond and the majestic peaks of Acadia. Indulge in their famous popovers and traditional New England fare as you savor the beauty of the park.

Day 4: Acadia National Park to White Mountains, New Hampshire

  • Morning: Depart from Acadia and journey towards the White Mountains of New Hampshire. Along the way, stop to explore charming coastal towns such as Bar Harbor, known for its quaint shops and stunning ocean views.

  • Afternoon: Arrive in the White Mountains and immerse yourself in the region's natural beauty, with visits to attractions such as the Flume Gorge and Franconia Notch State Park. Marvel at towering waterfalls, rugged cliffs, and pristine forests.

  • Evening: Treat yourself to a hearty dinner at the Woodstock Inn Station & Brewery, where you can sample locally brewed beers and classic New England dishes in a cozy, rustic atmosphere.

Day 5: White Mountains to Burlington, Vermont

  • Morning: Depart from the White Mountains and head west towards Burlington, Vermont. Make a stop in the charming town of Stowe to take a tour of the Ben & Jerry's Factory and indulge in some delicious ice cream.

  • Afternoon: Arrive in Burlington and explore the lively Church Street Marketplace, lined with eclectic shops, street performers, and outdoor cafes. Take in the vibrant atmosphere and soak up the local culture.

  • Evening: Dine at Hen of the Wood or The Farmhouse Tap & Grill, where you can enjoy farm-to-table cuisine made from fresh, locally sourced ingredients, paired with craft beers or artisanal cocktails.

Day 6: Burlington to Berkshires, Massachusetts

  • Morning: Depart from Burlington and journey south towards the Berkshires region of Massachusetts. Along the way, stop to admire picturesque covered bridges and scenic vistas.

  • Afternoon: Explore the cultural attractions of the Berkshires, such as the Norman Rockwell Museum, where you can view iconic American artworks, or Tanglewood, the summer home of the Boston Symphony Orchestra.

  • Evening: Enjoy a memorable dinner at the historic Old Mill Restaurant, nestled in the heart of the Berkshires. Indulge in classic New England fare and soak up the charm of this quintessential New England setting.

Day 7: Berkshires to Boston

  • Morning: Begin your journey back to Boston, with stops in quaint New England towns such as Stockbridge, known for its picturesque Main Street and historic landmarks.

  • Afternoon: Return to Boston and spend the afternoon exploring any missed attractions or indulging in some last-minute shopping in the upscale Back Bay neighborhood.

  • Evening: Conclude your New England road trip with a farewell dinner at The Union Oyster House, the oldest continuously operating restaurant in the United States. Enjoy fresh seafood and classic New England dishes in a historic setting, reflecting on the unforgettable experiences of your journey.


Top-rated Restaurants and Quick Stops:

  • Legal Sea Foods - Boston, Massachusetts

  • Neptune Oyster - Boston, Massachusetts

  • Eventide Oyster Co. - Portland, Maine

  • Street & Co. - Portland, Maine

  • Jordan Pond House - Acadia National Park, Maine

  • Woodstock Inn Station & Brewery - White Mountains, New Hampshire

  • Hen of the Wood - Burlington, Vermont

  • The Farmhouse Tap & Grill - Burlington, Vermont

  • Old Mill Restaurant - Berkshires, Massachusetts

  • The Union Oyster House - Boston, Massachusetts


Must-Do During the Road Trip:

  • Drive the Kancamagus Highway: Take in stunning views of the White Mountains on this scenic route through New Hampshire's wilderness.

  • Catch Sunrise at Cadillac Mountain: Experience the beauty of Acadia National Park as the sun rises over Cadillac Mountain, the first place to see daylight in the United States.

  • Explore Coastal Villages: Discover Maine's quaint coastal towns like Camden and Boothbay Harbor, where you can enjoy scenic harbors and fresh seafood.

  • Taste Maple Syrup in Vermont: Visit a local sugarhouse in Vermont to sample pure maple syrup and learn about the maple syrup-making process.

  • Attend a Clambake: Experience a traditional New England clambake, enjoying fresh seafood cooked over an open fire in the company of live music and good company.

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