The Ultimate 5 Day New England Road Trip Itinerary

Hello, fellow road trippers! Are you ready to embark on a picturesque journey through New England? This 5-day New England road trip itinerary is designed to show you the best of this region’s charming towns, stunning landscapes, and rich history. As someone who loves hitting the road and has a soft spot for New England’s unique allure, I’m thrilled to share this journey with you.

5 day New England road trip itinerary 2024

Day 1: Boston, Massachusetts – The Historic Start

Starting Point – Boston: Begin your New England adventure in Boston, a city steeped in history and culture. Spend your morning walking the Freedom Trail, a 2.5-mile route that takes you to 16 historically significant sites. Don’t miss the Boston Common, the United States’ oldest public park.

Afternoon Exploration: In the afternoon, explore the cobblestone streets of Beacon Hill, known for its beautiful Federal-style rowhouses and quaint atmosphere. Enjoy a meal at one of the local eateries – Boston’s culinary scene is a delightful mix of traditional New England fare and modern cuisine.

Evening in Boston: As evening falls, head to the Boston Harbor or stroll along the Charles River Esplanade for stunning city views.

Boston, 5 Day New England Road Trip Itinerary

Day 2: Boston to Cape Cod, Massachusetts – Coastal Charm

Morning Drive to Cape Cod: On your second day, head to Cape Cod, a hook-shaped peninsula known for its quaint villages, seafood shacks, Martha’s vineyard and lighthouses. The drive from Boston to Cape Cod is about 1.5 hours, but take your time and enjoy the scenic journey.

Exploring Cape Cod: Once in Cape Cod, visit the Cape Cod National Seashore for its beautiful beaches and walking trails. Check out Provincetown for its art galleries and vibrant street life.

Overnight in Cape Cod: Spend the night in one of Cape Cod’s charming inns or bed and breakfasts, experiencing true New England hospitality.

5 Day New England Road Trip Itinerary, Cape Cod

Day 3: Cape Cod to Newport, Rhode Island – A Touch of Elegance

Journey to Newport: On day three, travel to Newport, Rhode Island, renowned for its stunning Gilded Age mansions and sailing culture. The drive takes about 1.5 hours, offering beautiful coastal views along the way.

Discovering Newport: In Newport, tour The Breakers, the grandest of Newport’s summer “cottages” and a symbol of the Vanderbilt family’s social and financial preeminence in the Gilded Age. Stroll along the Cliff Walk, a 3.5-mile path that offers spectacular ocean views on one side and opulent mansions on the other.

Evening Leisure: Enjoy an evening in Newport’s historic downtown, dining by the waterfront and savoring fresh local seafood.

Newport, 5 day New England Road trip itinerary

Day 4: Newport, Rhode Island to White Mountains, New Hampshire – Into the Wilderness

Morning in Newport: Start your fourth day with a leisurely morning in Newport. Perhaps take a sail around Narragansett Bay or explore more of the town’s historic streets and shops.

Drive to the White Mountains: Mid-morning, begin your journey north to the White Mountains in New Hampshire. This drive takes you into the heart of New England’s natural beauty. The journey is about 4 hours but feels shorter due to the stunning scenery along the way.

Exploring the White Mountains: Upon arrival, immerse yourself in the natural splendor of the White Mountains. Visit Franconia Notch State Park, where you can see the Flume Gorge, a natural granite gorge extending 800 feet at the base of Mount Liberty. The Cannon Mountain Aerial Tramway offers breathtaking panoramic views.

Overnight in the Mountains: Spend your night in a cozy mountain lodge or cabin. The White Mountains region offers various accommodations, from rustic to luxurious, allowing you to enjoy the serene mountain atmosphere.

Flume Gorge, 5 Day New England Road Trip Itinerary

Day 5: White Mountains to Portland, Maine – A Coastal Finale

Morning Hikes and Scenic Views: Wake up early to catch a sunrise in the mountains. If you’re up for it, enjoy a morning hike; there are trails for all skill levels, offering one last chance to soak in the natural beauty of New Hampshire.

Journey to Portland, Maine: After your morning in the mountains, set off for Portland, Maine, about a 2-hour drive. This charming coastal city is known for its vibrant arts scene, historic Old Port waterfront, and incredible seafood.

Discovering Portland: Spend your afternoon exploring Portland’s cobblestone streets, unique boutiques, and art galleries. The Portland Head Light, a historic lighthouse in nearby Cape Elizabeth, is worth a visit for its picturesque setting.

Evening in Portland: Conclude your New England road trip with a delightful dinner in Portland. The city’s culinary scene is a fusion of traditional New England flavors and innovative cuisine. Enjoy a meal at one of the waterfront restaurants, savoring the fresh catch of the day.

Portland 5 day New England Travel itinerary

Reflecting on Your New England Road Trip

Your 5-day New England road trip itinerary has taken you on a journey through some of the most picturesque and culturally rich parts of the Northeast. From the historic streets of Boston to the coastal beauty of Cape Cod and Newport, the majestic White Mountains, and the charming city of Portland, you’ve experienced a tapestry of landscapes and lifestyles that make New England unique.

As you head home, you carry with you not just photos but memories of quaint towns, scenic drives, and the warm hospitality of the Northeast. This trip is more than just a journey through places; it’s an exploration of the heart and soul of New England.

I hope this itinerary inspires you to explore the diverse beauty of New England. Safe travels, and may your road trips be filled with discovery and joy. If you need any more tips or insights for traveling in New England or beyond, feel free to reach out. Happy travels!

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