Best Ideas for a 5-Day New England Road Trip Itinerary

Dreaming of a picturesque autumn escape? Picture this: a 5-day road trip through New England’s six diverse states, ablaze with vibrant fall foliage. From Boston’s historic streets to Maine’s rugged coast, New Hampshire’s majestic mountains, Vermont’s charming towns, and the artistic Berkshires, this itinerary offers an unforgettable experience. Explore top attractions, savor fresh seafood, hike scenic trails, and discover local treasures. Start planning your New England adventure today!

Important information

• This road trip covers six states: Maine, New Hampshire, Vermont, Massachusetts, Connecticut, and Rhode Island.
• Late September to mid-October offers the most vibrant fall foliage.
• Key destinations include Boston for history, Portland, ME for seafood, the White Mountains for scenic drives and hikes, Stowe, VT for outdoor activities, and the Berkshires for culture.
• Driving is recommended, but be prepared for traffic and changing weather, especially in the mountains. Pack layers, rain gear, and download offline maps.
• Consider unique lodging like glamping in yurts, cabins, or treehouses for a memorable experience.

Introduction to Planning a 5-Day New England Road Trip

Embark on an unforgettable 5-day road trip through New England, where history, nature, and breathtaking coastlines converge. Explore six diverse states: Maine, New Hampshire, Vermont, Massachusetts, Connecticut, and Rhode Island—all within easy driving distance. Discover charming towns and diverse landscapes, making for a smooth and memorable journey.

Why Choose New England for a Road Trip?

Best Time to Visit for Fall Foliage

Plan your visit to New England between late September and mid-October for the most vibrant fall foliage. This period offers a spectacular display of color.

Day 1: Start Your Journey in Boston

Embark on your New England adventure in Boston, Massachusetts, a city renowned for its rich history and vibrant culture. Discover Boston’s must-see attractions and captivating neighborhoods.

Exploring Historical Attractions

Discover Boston, a city rich in American history and brimming with captivating attractions. Follow the Freedom Trail to encounter iconic landmarks such as Paul Revere’s House and the Boston Massacre site, each offering a profound glimpse into the nation’s past. Immerse yourself in the lively atmosphere of Faneuil Hall Marketplace, and then unwind amidst the serene beauty of Boston Common. For a truly engaging experience, delve into the pivotal moment in history at the Boston Tea Party Ships & Museum.

Local Cuisine and Food Recommendations

Boston, a seafood lover’s paradise, offers incredible New England classics. Indulge in creamy clam chowder, fresh lobster rolls, and delectable oysters. For dessert, savor a slice of Boston cream pie or a rich cannoli.

Day 2: Scenic Drive to Portland, Maine

Embark on a scenic drive to Portland, Maine on your second day, enjoying picturesque coastal vistas and charming towns along the way. Consider a stop in Portsmouth, New Hampshire, to admire the historic architecture and explore its lively waterfront.Portland is renowned for its vibrant arts scene and the historic Old Port district. Fresh seafood is a local staple, and the iconic Portland Head Light is a must-see. Don’t miss the opportunity to sample the superb local craft brews.

Must-See Coastal Towns

Explore these New England destinations and uncover their individual charm.

Where to Enjoy Lobster Rolls and Clam Cakes

Portland, Maine, is famous for its lobster rolls and clam cakes, but these New England treats can be found all along the coast. some popular spots include Red’s Eats in Wiscasset, Bob’s Clam Hut in Kittery, and The Clam Shack in Kennebunkport. For broader menus, try J.T.’s Ocean View Seafood Shack in Portland or the Bite into Maine food truck. Eventide Oyster Co., also in Portland, offers a modern twist on seafood favorites.

Day 3: Discover the White Mountains of New Hampshire

Embark on a captivating journey through New Hampshire’s White Mountains on day three, immersing yourself in breathtaking scenery. A must-see is Franconia Notch State Park, where you can marvel at the Flume Gorge and ascend the Cannon Mountain Aerial Tramway for panoramic vistas. Hiking enthusiasts can challenge themselves on the Appalachian Trail or conquer Mount Washington, the Northeast’s highest peak. For a more relaxed experience, the Kancamagus Highway offers a stunning scenic drive, especially vibrant during the fall foliage season. Discover the charm of towns like North Conway, known for its shopping, dining, covered bridges, and local culture.

Exploring the Kancamagus Highway

The 34.5-mile Kancamagus Highway (Route 112) in New Hampshire is a scenic byway renowned for its breathtaking views, particularly striking during peak foliage season. Winding through the White Mountain National Forest, the highway offers numerous overlooks with stunning vistas. For those seeking a closer look at nature, various hiking trails are accessible from the highway, and picnic areas provide spots for a relaxing break.

Peak Foliage and Hiking Trails

Experience the vibrant fall foliage of the White Mountains in early to mid-October. Hike through a diverse network of trails, from leisurely strolls to challenging climbs. For stunning views, explore Flume Gorge, ascend Mount Washington, or visit the Appalachian Trail and Franconia Notch State Park. Alternatively, enjoy a scenic drive along the Kancamagus Highway.

Day 4: Vermont Adventures in Stowe and Beyond

Charming Small Towns and Scenic Byways

Stowe, Vermont, is a skier’s dream, centered around the renowned Stowe Mountain Resort. Beyond the slopes, explore the scenic Route 100 byway, offering breathtaking vistas. A picturesque drive will lead you through charming villages like Weston and Waitsfield, home to craft breweries and art galleries. Discover Vermont’s iconic covered bridges and, for a fun and informative experience, tour the Ben & Jerry’s factory in nearby Waterbury.

Outdoor Activities and Leaf Peeping

Experience Stowe’s stunning fall foliage with a variety of activities. Hike through the vibrant colors of Smugglers’ Notch State Park and Mount Mansfield State Forest. For a unique perspective, bike the Stowe Recreation Path, enjoying the picturesque scenery. Alternatively, take a relaxing drive along scenic Route 100 or other byways offering breathtaking views. A fall trip to Stowe promises unforgettable memories.

Day 5: Conclude Your Trip in Southern Vermont and The Berkshires

Embark on a captivating journey through the picturesque Litchfield Hills, renowned for its charming villages, rolling landscapes, and breathtaking drives. Begin your adventure in Kent, Connecticut, a historic town brimming with antique shops and art galleries. Immerse yourself in nature at Kent Falls State Park, where you can hike scenic trails and marvel at cascading waterfalls.

Exploring Litchfield Hills

Litchfield Hills, located in northwestern Connecticut, is famous for its beautiful scenery of rolling hills and charming towns. Outdoor activities abound, including hiking, biking, and kayaking, while scenic drives provide breathtaking views. The area also boasts antique shops and art galleries, adding to its allure and making it an ideal destination for exploration.

Where to Enjoy Blueberry Pancakes

Indulge your blueberry pancake cravings in Southern Vermont and The Berkshires. Bennington, Vermont’s aptly named Pancake House is famous for its classic blueberry pancakes. A short drive away in Pittsfield, Massachusetts, Dottie’s Coffee Lounge offers diverse blueberry pancake creations featuring fresh, locally sourced berries. Other delightful options include PJ’s Pancake House, Brenda’s Busy Bee Cafe, The Red Lion Inn, and Saxy’s Cafe, each putting a unique spin on this beloved breakfast dish.

Accommodation Options in New England

Planning a family getaway? New England offers diverse lodging options, from cozy guesthouses for a comfortable stay to unique glamping adventures immersed in nature. Find the perfect blend of budget, style, and experience.

Family-Friendly Guesthouses

Family-friendly guesthouses offer several amenities to simplify traveling with children. These amenities often include cribs, high chairs, play areas, and sometimes even organized activities. Parents can relax in communal spaces while their children play. The locations are often conveniently situated near family attractions such as parks, museums, and beaches. Flexible dining options also cater to children’s needs, ensuring a comfortable and enjoyable stay for the whole family.

Unique Glamping Experiences

Experience the best of both worlds with glamping, a glamorous take on traditional camping. Enjoy luxurious amenities like comfortable beds, electricity, and even Wi-Fi, all while immersed in nature. For a truly unique stay, try lodging in yurts, cabins, or treehouses.

Embrace the beauty of the outdoors without sacrificing comfort.

Travel Tips for a Successful New England Road Trip

Planning a New England road trip? Here’s how to make it unforgettable.

How to Get Around New England

Exploring New England by car offers the freedom to discover hidden gems along the way. While a flexible itinerary is recommended, be mindful of traffic, particularly during peak seasons. For a more scenic experience, consider venturing onto the backroads, which often reveal breathtaking vistas. Remember that mountain weather can change rapidly, so it’s always best to be prepared.

Packing List Essentials