Road Trips in New England: 10 Best Year-Round Itineraries, Start, End, Distances & Suitable Season

Embarking on a road trip through New England is like journeying through a living postcard, where every twist and turn reveals breathtaking landscapes, rich history, and vivid culture. 

This charming region of the United States, comprising six northeastern states – Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont – offers an unparalleled diversity of experiences year-round. 

Whether you’re exploring the rugged coastline of Maine, meandering through the scenic countryside of Vermont, or immersing yourself in the rich colonial heritage of Massachusetts, each route promises unforgettable adventures. 

From the vivid fall foliage to the tranquil beauty of snow-covered landscapes, New England’s ever-changing scenery provides the perfect backdrop for road trip enthusiasts. 

Whether you’re seeking outdoor adventures, historic landmarks, or quaint coastal towns, New England’s winding roads and scenic byways offer endless opportunities for exploration and discovery. 

So, buckle up and get ready to embark on an unforgettable journey through one of America’s most picturesque regions.

10 Best Year-Round Road Trip Itineraries in New England

Exploring New England by road is a journey through stunning landscapes, rich history, and vivid culture. 

With its charming coastal towns, picturesque countryside, and majestic mountains, New England offers an abundance of year-round road trip itineraries.

Here are 10 of the best:

1. Coastal Maine Loop

Coastal Maine Loop

Begin your journey in Portland, Maine’s largest city, known for its vivid food scene and historic waterfront. 

As you head northeast along the coast, stop by the charming town of Kennebunkport, famous for its sandy beaches and upscale boutiques. 

Further up the coast, immerse yourself in the picturesque beauty of Camden, where you can sail along the Penobscot Bay or hike Camden Hills State Park for panoramic views. 

Finally, reach Acadia National Park, where the rugged coastline, granite peaks, and diverse wildlife await exploration. 

Don’t miss hiking Cadillac Mountain for stunning sunrise views or enjoying a traditional lobster bake in Bar Harbor.

Start: Portland, Maine

End: Acadia National Park/Bar Harbor, Maine

Distance: Approximately 230 miles

Suitable Season: Spring, Summer, Fall

2. Vermont Scenic Byways

Vermont Scenic Byways

Vermont’s scenic byways offer a journey through quintessential New England landscapes. Start your adventure in Stowe, a charming town being at the foot of Mount Mansfield, the state’s highest peak. 

From there, follow Route 100, known as the “Skiers’ Highway,” passing through idyllic villages, historic covered bridges, and rolling farmland. 

Make sure to stop by Waterbury to tour the Ben & Jerry’s Ice Cream Factory and visit the quaint village of Manchester for its upscale outlets and scenic vistas of the Green Mountains.

Start: Stowe, Vermont

End: Manchester, Vermont

Distance: Varies depending on the chosen route (approximately 200-250 miles)

Suitable Season: Spring, Summer, Fall

3. White Mountains Circuit (New Hampshire)

White Mountains Circuit

Begin your exploration in North Conway, a bustling town surrounded by the stunning peaks of the White Mountains. 

Embark on the scenic Kancamagus Highway, winding through the heart of the White Mountain National Forest, offering breathtaking views of autumn foliage or snow-capped peaks, depending on the season. 

Along the way, take a thrilling ride on the Mount Washington Auto Road or ascend to the summit aboard the historic cog railway. 

Afterward, unwind in the charming town of Lincoln, home to the iconic Clark’s Trading Post and the Loon Mountain Resort.

Start: North Conway, New Hampshire

End: Lincoln, New Hampshire

Distance: Approximately 100 miles

Suitable Season: Summer, Fall

4. Connecticut River Valley

Connecticut River Valley

Follow the tranquil path of the Connecticut River as it meanders through the picturesque countryside of Massachusetts and Vermont. 

Start your journey in Northfield, Massachusetts, home to the historic campus of Northfield Mount Hermon School. 

Continue northward, passing through charming towns like Shelburne Falls, known for its scenic Bridge of Flowers spanning the Deerfield River. 

Explore the vivid arts scene of Northampton before crossing into Vermont, where you can visit attractions like the Vermont Country Store in Weston or take a scenic drive along Route 30, known as the “Vermont Cheese Trail.”

Start: Northfield, Massachusetts

End: Weston, Vermont

Distance: Approximately 100-150 miles

Suitable Season: Spring, Summer, Fall

5. Rhode Island Coastal Drive

 Rhode Island Coastal Drive

Explore the scenic beauty of the Ocean State along its picturesque coastline. Begin your journey in Newport, renowned for its opulent Gilded Age mansions and historic waterfront. 

Take a leisurely drive along Ocean Drive, offering panoramic views of the Atlantic Ocean and iconic landmarks like the Newport Cliff Walk. 

Continue your coastal exploration to the charming village of Watch Hill, where you can relax on pristine beaches or visit the historic Flying Horse Carousel. 

Conclude your journey at Beavertail State Park, located on the southern tip of Jamestown, offering stunning views of Narragansett Bay and the surrounding coastline.

Start: Newport, Rhode Island

End: Beavertail State Park, Rhode Island

Distance: Approximately 50 miles

Suitable Season: Spring, Summer, Fall

6. Massachusetts Berkshire Loop

Massachusetts Berkshire Loop

Explore the cultural and natural wonders of the Berkshires in western Massachusetts. Begin in Lenox, home to the renowned Tanglewood Music Center, where you can enjoy world-class performances amid picturesque surroundings. 

Visit the Norman Rockwell Museum in Stockbridge to admire the iconic works of this celebrated American artist. 

Don’t miss the opportunity to hike to the summit of Mount Greylock, the highest point in Massachusetts, for sweeping views of the surrounding landscape.

Start: Lenox, Massachusetts

End: Lenox, Massachusetts

Distance: Approximately 100 miles

Suitable Season: Spring, Summer, Fall

7. Maine’s Lakes and Mountains

Maine's Lakes and Mountains

Discover the serene beauty of Maine’s interior as you traverse through the Lakes and Mountains region. Start your journey in Bethel, a charming town in the foothills of the White Mountains. 

Explore the outdoor paradise of Sunday River Resort, offering skiing in the winter and hiking and biking trails in the summer. 

Continue your adventure to Rangeley Lake State Park, where you can enjoy boating, fishing, and wildlife watching amidst pristine wilderness.

Start: Bethel, Maine

End: Rangeley, Maine

Distance: Approximately 100 miles

Suitable Season: Spring, Summer, Fall

8. Cape Cod and the Islands

Cape Cod and the Islands

Experience the quintessential charm of Cape Cod and the nearby islands of Martha’s Vineyard and Nantucket. Begin your journey in Hyannis, a bustling town known for its maritime history and scenic harbor. 

Explore the quaint villages of Chatham and Provincetown, where you can stroll along picturesque streets lined with historic homes and art galleries. 

Take a ferry to Martha’s Vineyard and Nantucket to soak in the relaxed island atmosphere and pristine beaches.

Start: Hyannis, Massachusetts

End: Nantucket or Martha’s Vineyard, Massachusetts

Distance: Varies depending on ferry routes (approximately 50-100 miles)

Suitable Season: Spring, Summer, Fall

9. Acadia and the Maine Coast

Acadia and the Maine Coast

Immerse yourself in the rugged beauty of Maine’s coastline and Acadia National Park. Start your adventure in Bar Harbor, the gateway to Acadia, where you can explore the charming downtown area and sample fresh seafood delicacies. 

Spend your days hiking scenic trails, biking along carriage roads, or kayaking along the rocky shores. 

Don’t miss the chance to drive along Route 1, stopping in quaint coastal towns like Camden and Rockland for a taste of quintessential Maine.

Start: Bar Harbor, Maine

End: Camden/Rockland, Maine

Distance: Approximately 150-200 miles

Suitable Season: Spring, Summer, Fall

10. Northern New England Loop

Northern New England Loop

Embark on a scenic journey through the northern reaches of New England, starting in Burlington, Vermont. Explore the vivid arts scene and culinary delights of Burlington before heading east into the picturesque countryside. 

Drive through the scenic beauty of the Northeast Kingdom, known for its rolling hills and pristine lakes. Cross into New Hampshire and Maine, where you can explore charming towns, scenic byways, and outdoor adventures amidst breathtaking landscapes.

Start: Burlington, Vermont

Distance: Approximately 200-300 miles

Suitable Season: Spring, Summer, Fall


How many days do you need to see New England?

A comprehensive exploration typically requires 7 to 10 days, but shorter visits of 3 to 5 days can still provide a taste of the region.

What is the best road trip to take in New England?

Popular options include the Coastal Maine Loop, Vermont Scenic Byways, and the White Mountains Circuit, each offering unique charm.

What month is best for road trips in New England?

It varies, with fall (September and October) renowned for foliage, spring and summer ideal for outdoor activities, and winter perfect for skiing.

Wrap Up

Road tripping through New England is an enriching experience that offers a tapestry of natural beauty, rich history, and vivid culture. 

From the rugged coastlines of Maine to the picturesque mountains of Vermont, every journey unveils new adventures and timeless landscapes. 

Whether you’re indulging in fresh seafood along the coastal routes or exploring historic towns steeped in colonial heritage, New England’s winding roads and scenic byways never fail to captivate. 

With each season offering its own unique charm, a road trip in New England promises unforgettable memories and endless opportunities for discovery in one of America’s most picturesque regions.

Photo of author

Naim Benmayor

I am a passionate and knowledgeable tour guide at Boston Private Guide, dedicated to providing you with an unforgettable experience in the historic city of Boston. With years of expertise, I bring the rich history, culture, and hidden gems of this vibrant city to life. Whether you're interested in exploring the Freedom Trail, indulging in the culinary delights of the North End, or discovering the lesser-known stories of Boston's past, I am here to tailor a personalized tour just for you. Join me on a journey through Boston's streets, where every cobblestone has a tale to tell, and let's create lasting memories together. LinkedIn

Leave a Comment