Introduction
Embarking on a road trip is a fantastic way to explore the picturesque landscapes, charming towns, and rich history of the New England region. With its vibrant fall foliage, quaint coastal villages, and historic landmarks, New England offers endless possibilities for the perfect itinerary.
Whether you’re a nature lover, a history buff, or simply seeking a relaxing getaway, New England has something to offer everyone. From the rugged coastline of Maine to the scenic beauty of Vermont, and the charming towns of Massachusetts and Connecticut, there’s no shortage of hidden gems waiting to be discovered.
In this article, we’ve curated a collection of 12 epic road trip itineraries that will take you on a journey through the best of New England. Each itinerary is designed to showcase the unique attractions and experiences of the region, ensuring that you have an unforgettable adventure.
As you embark on your New England road trip, keep in mind that flexibility is key. These itineraries provide a framework for your journey, but don’t be afraid to deviate from them and explore off the beaten path. After all, some of the best memories are made when you stumble upon unexpected treasures.
Get ready to hit the road and immerse yourself in the natural beauty, rich history, and warm hospitality that New England is known for. Pack your bags, fuel up the car, and let’s begin our journey through the scenic wonders of this captivating region.
Road Trip #1: The Best of Coastal Maine
Prepare to be enchanted as you embark on a breathtaking road trip along the stunning coastline of Maine. This itinerary will take you through charming seaside towns, picturesque lighthouses, and some of the most breathtaking natural landscapes in New England.
Start your journey in the vibrant city of Portland, known for its bustling food scene and historic Old Port district. Explore the cobblestone streets, visit the Portland Head Light, one of the most iconic lighthouses in the country, and indulge in fresh seafood at the acclaimed local eateries.
Next, make your way to the quaint town of Kennebunkport, where you can stroll along the scenic shores of Goose Rocks Beach and admire the beautiful mansions along Ocean Avenue. Don’t forget to stop by Dock Square for some shopping and a taste of the famous lobster rolls.
Continue your coastal adventure by heading north to Acadia National Park. This national treasure offers unparalleled beauty with its rugged coastline, towering granite cliffs, and miles of hiking trails. Take a scenic drive along Park Loop Road, hike up to the summit of Cadillac Mountain for breathtaking views, and enjoy the serenity of Jordan Pond.
As you continue up the coast, don’t miss the charming town of Bar Harbor. Home to charming bed and breakfasts, unique shops, and mouthwatering seafood, it’s the perfect place to relax and soak in the coastal ambiance.
Further north, discover the beauty of the Midcoast region. Visit the picturesque town of Camden, known for its picturesque harbor and iconic Camden Hills State Park. Climb to the top of Mount Battie for panoramic views of the surrounding islands and coastline.
End your journey in the stunning Acadia National Park. Explore the rocky shores, hike the scenic trails, and savor the tranquility of this natural wonderland.
From Portland to Acadia National Park, this road trip through coastal Maine is sure to leave you with unforgettable memories of picturesque landscapes, delicious seafood, and the warm hospitality of New England.
Road Trip #2: Discovering Historic Massachusetts
Step back in time as you embark on a road trip through the historic state of Massachusetts. From the birthplace of the American Revolution to the charming coastal towns, this itinerary will immerse you in the rich history and cultural landmarks that define this captivating state.
Start your journey in the city of Boston, where you can explore the iconic Freedom Trail. Follow the red brick path that winds through the city, taking you to significant historical sites such as the Paul Revere House, the Old North Church, and the Massachusetts State House. Don’t miss the opportunity to stroll along the lively waterfront at Boston Harbor.
Next, head west to Lexington and Concord, where the first shots of the American Revolution were fired. Visit the Lexington Battle Green, the Minute Man National Historical Park, and the Old North Bridge to experience the sites that shaped American history.
Continue your road trip south to Cape Cod, a peninsula known for its scenic beauty and charming seaside towns. Explore the vibrant art scene in Provincetown, relax on the pristine beaches of Chatham, and indulge in fresh seafood in Wellfleet.
As you make your way back towards Boston, take a detour to Salem, famous for the Salem witch trials of 1692. Immerse yourself in the history of this intriguing town by visiting the Salem Witch Museum, the Witch House, and the Peabody Essex Museum.
Wrap up your journey with a visit to Plymouth, the landing site of the Pilgrims in 1620. Explore the living history museum at Plimoth Plantation, step aboard the Mayflower II replica, and visit the iconic Plymouth Rock.
From the bustling streets of Boston to the quaint coastal towns and historic landmarks, this road trip through Massachusetts will transport you back in time and leave you with a deeper appreciation for the rich history and culture of this remarkable state.
Road Trip #3: Scenic Beauty in Vermont
Prepare to be captivated by the picturesque landscapes of Vermont as you embark on a road trip through this stunning New England state. Known for its charming small towns, scenic countryside, and vibrant fall foliage, Vermont offers a serene and idyllic setting for a memorable journey.
Start your adventure in the charming town of Burlington, located on the shores of Lake Champlain. Explore the vibrant Church Street Marketplace, visit the beautiful Shelburne Museum, and take a scenic bike ride along the Burlington Bike Path.
Next, head south to the historic town of Middlebury, home to Middlebury College and breathtaking views of the Green Mountains. Take a leisurely stroll along the Middlebury Riverwalk, visit the picturesque campus, and enjoy a drive through the nearby countryside.
Continue your journey through Vermont by heading to Stowe, a popular destination for outdoor enthusiasts and nature lovers. Explore the stunning beauty of Smugglers’ Notch State Park, hike to the summit of Mount Mansfield, and indulge in the charming shops and restaurants in the downtown area.
As you make your way across the state, don’t miss a visit to Woodstock, often considered one of the prettiest towns in Vermont. Admire the classic New England architecture, visit the Billings Farm and Museum, and take a scenic drive through the surrounding countryside.
Continue your exploration of Vermont’s natural beauty by venturing to the Northeast Kingdom, a region known for its untouched wilderness and breathtaking views. Visit Lake Willoughby, hike in the stunning Groton State Forest, and immerse yourself in the tranquility of this pristine area.
Wrap up your road trip with a visit to Bennington, located in the southwestern part of Vermont. Explore the iconic Bennington Battle Monument, visit the Bennington Museum, and enjoy a leisurely stroll through the charming downtown area.
From vibrant towns to serene landscapes, this road trip through Vermont will leave you in awe of the state’s scenic beauty and welcoming atmosphere. So, pack your bags, hit the open road, and let Vermont’s charm surround you on this unforgettable journey.
Road Trip #4: Exploring the White Mountains in New Hampshire
Embark on a thrilling adventure through the majestic White Mountains of New Hampshire. This road trip will take you through breathtaking landscapes, charming towns, and outdoor activities that will leave you in awe of this natural wonderland.
Your journey begins in the town of North Conway, known for its scenic beauty and outdoor recreation opportunities. Explore the quaint village filled with shops, restaurants, and galleries. Take a scenic drive on the Kancamagus Highway, known as one of the most beautiful drives in New England, and marvel at the stunning fall foliage.
Continue your road trip by visiting Franconia Notch State Park, home to the iconic Flume Gorge and Cannon Mountain. Hike through the breathtaking gorge, ride the aerial tramway to the summit of Cannon Mountain for panoramic views, and explore the numerous hiking trails in the area.
Next, make your way to the picturesque town of Lincoln, where you can visit the popular attractions of Clark’s Trading Post and the Lost River Gorge and Boulder Caves. Enjoy the beautiful scenery and outdoor activities such as hiking, biking, and kayaking in the surrounding White Mountain National Forest.
Continue your journey by exploring the town of Jackson, known for its classic New England charm. Take a scenic drive along the famous Jackson Covered Bridge, hike the trails in the White Mountain National Forest, and enjoy the stunning views of Mount Washington, the highest peak in the Northeast.
As you make your way towards the end of your road trip, don’t miss the opportunity to visit the charming town of Portsmouth. Explore the historic downtown area, visit the Strawberry Banke Museum, and indulge in fresh seafood along the waterfront.
From the breathtaking landscapes of the White Mountains to the charming towns along the way, this road trip through New Hampshire will immerse you in the beauty and natural wonders of this remarkable region. So, grab your camera, pack your hiking boots, and get ready for an unforgettable journey through the White Mountains.
Road Trip #5: Connecticut’s Hidden Gems
Prepare to uncover the hidden gems of Connecticut as you embark on a road trip through this underrated New England state. From charming coastal towns to picturesque countryside, this itinerary will take you off the beaten path and introduce you to the lesser-known treasures of Connecticut.
Start your journey in Mystic, a historic maritime town known for its quaint charm and rich seafaring history. Explore the Mystic Seaport Museum, take a scenic cruise on the historic Mystic River, and indulge in fresh seafood at the local restaurants.
Next, venture to the quaint town of Essex, located along the Connecticut River. Admire the well-preserved colonial buildings, take a leisurely stroll along the charming Main Street, and visit the Connecticut River Museum to learn about the area’s maritime heritage.
Continue your road trip by heading to the picturesque town of Kent, nestled in the foothills of the Berkshire Mountains. Explore the Kent Falls State Park, hike the scenic trails in Macedonia Brook State Park, and browse the unique shops and galleries in the downtown area.
As you make your way to the coast, don’t miss a visit to the charming town of Guilford. Stroll along the town green, visit the historic Faulkner’s Island Lighthouse, and enjoy the beautiful shoreline at Guilford Point Beach.
Continue your coastal exploration by heading to the town of Stonington, located on the Connecticut-Rhode Island border. Visit the scenic Stonington Point, explore the charming downtown area, and take a sunset cruise on the Mystic River to admire the stunning coastal views.
Wrap up your journey with a visit to the vibrant city of New Haven. Explore the prestigious Yale University campus, stroll through the beautiful Yale University Art Gallery, and indulge in world-class pizza at one of the famous New Haven pizzerias.
From Mystic to New Haven, this road trip through Connecticut will introduce you to the hidden gems of the state and leave you with a newfound appreciation for its unique blend of history, natural beauty, and coastal charm.
Road Trip #6: Rhode Island’s Coastal Charm
Get ready to experience the coastal charm of Rhode Island as you embark on a road trip through the scenic wonders of the Ocean State. From beautiful beaches to historic towns, this itinerary will highlight the unique attractions and captivating coastal landscapes that Rhode Island has to offer.
Start your journey in the vibrant city of Providence, known for its rich cultural heritage and thriving arts scene. Explore the charming streets of the Downcity district, visit the prestigious Brown University campus, and take a stroll along the picturesque Waterplace Park.
Next, make your way to Newport, a picturesque coastal town renowned for its opulent mansions and maritime history. Take a tour of the grand Newport mansions, such as The Breakers and Marble House, enjoy a leisurely walk along the Cliff Walk, and visit the historic Newport Harbor.
Continue your coastal adventure by heading to Narragansett, a popular beach destination. Spend a day lounging on the beautiful Narragansett Town Beach, explore the trails at the picturesque Beavertail State Park, and indulge in delicious seafood at one of the local waterfront restaurants.
As you make your way along the coast, don’t miss a visit to the charming town of Block Island. Take a ferry ride to this idyllic island and explore its picturesque beaches, scenic bike paths, and the iconic Block Island Southeast Light.
Continue your road trip by heading to the town of Watch Hill, known for its stunning beaches and the historic Watch Hill Lighthouse. Enjoy a day of relaxation on the sandy shores, visit the enchanting Flying Horse Carousel, and take a stroll along the charming Water Street.
Wrap up your coastal exploration with a visit to the town of Jamestown, located on Conanicut Island. Enjoy panoramic views of Narragansett Bay from Beavertail State Park, visit the historic Jamestown Windmill, and take a leisurely drive along the scenic Ocean Drive.
From Providence to Jamestown, this road trip through Rhode Island will mesmerize you with its coastal charm, beautiful beaches, and rich history. So, pack your sunscreen, embrace the coastal breeze, and get ready for an unforgettable journey through the enchanting Ocean State.
Road Trip #7: Captivating Cape Cod
Get ready to be enchanted by the idyllic beauty of Cape Cod as you embark on a road trip through this beloved New England destination. With its charming coastal towns, stunning beaches, and picturesque scenery, Cape Cod offers a quintessential New England experience.
Your journey starts in the charming town of Falmouth. Explore the historic streets, visit the iconic Nobska Lighthouse, and take a scenic ferry ride to Martha’s Vineyard for a day of exploring the beautiful island.
Next, head east to the vibrant town of Hyannis, known for its maritime heritage and connection to the Kennedy family. Visit the John F. Kennedy Hyannis Museum, take a stroll along the picturesque Hyannis Harbor, and indulge in fresh seafood at the local restaurants.
Continue your road trip by exploring the picturesque town of Chatham. Relax on the stunning beaches, visit the Chatham Lighthouse, and take a scenic walk along Main Street lined with boutiques, art galleries, and charming cafes.
As you make your way to the outer cape, don’t miss a visit to the breathtaking Cape Cod National Seashore in Eastham. Explore the stunning beaches, hike the scenic trails, and take in the preserved natural beauty of this remarkable area.
Continue your coastal adventure by heading to Provincetown, a vibrant and eclectic town at the tip of Cape Cod. Explore the art galleries, visit the iconic Pilgrim Monument, and take a whale-watching excursion to witness these majestic creatures up close.
Wrap up your journey with a visit to the charming town of Sandwich, known for its quaint charm and historic attractions. Visit the famous Sandwich Glass Museum, explore the Heritage Museums and Gardens, and enjoy a leisurely stroll along the picturesque boardwalk.
From Falmouth to Sandwich, this road trip through Cape Cod will captivate you with its scenic beauty, historic charm, and coastal allure. So, pack your beach gear, prepare for relaxation, and get ready to experience the captivating charm of Cape Cod.
Road Trip #8: Charming Vermont Towns
Immerse yourself in the charm and beauty of Vermont as you embark on a road trip through its idyllic towns. Known for its picturesque landscapes, charming architecture, and warm hospitality, Vermont offers a delightful journey through its many charming towns.
Start your adventure in the town of Stowe, nestled in the Green Mountains. Explore the quaint village lined with charming shops and eateries, take a scenic drive along the stunning Mountain Road, and visit the iconic Trapp Family Lodge, home of the famous Sound of Music family.
Next, make your way to the town of Woodstock, often hailed as one of the prettiest small towns in America. Take a leisurely stroll along the charming Main Street, visit the Billings Farm and Museum, and admire the historic architecture of the Woodstock Inn.
Continue your journey to Manchester, known for its sophisticated ambiance and upscale shops. Explore the designer outlets, visit the famous Hildene estate, and take a scenic hike along the Equinox Mountain trails for breathtaking views.
As you make your way through Vermont, don’t miss a visit to the town of Bennington. Admire the striking Bennington Battle Monument, visit the vibrant Bennington Museum, and enjoy a walk through the charming downtown area.
Next, venture to the town of Middlebury, home to Middlebury College and surrounded by stunning countryside. Take a leisurely stroll along the Middlebury Riverwalk, visit the beautiful college campus, and explore the charming shops and galleries.
Wrap up your journey in the town of Burlington, located on the shores of Lake Champlain. Explore the vibrant Church Street Marketplace, visit the impressive University of Vermont campus, and enjoy the beautiful waterfront views.
From Stowe to Burlington, this road trip through Vermont showcases the state’s charming towns and warm hospitality. So, hit the road, embrace the scenic beauty, and immerse yourself in the delightful charm of Vermont’s idyllic towns.
Road Trip #9: Fall Foliage Spectacular in New England
Experience the breathtaking beauty of autumn in New England as you embark on a road trip through the region’s renowned fall foliage. This itinerary will take you through the scenic landscapes of Vermont, New Hampshire, and Massachusetts, showcasing the vibrant colors and stunning foliage that make this season so special.
Your journey begins in the charming town of Stowe, Vermont, known for its picturesque vistas and stunning fall colors. Take a scenic drive along the renowned Smugglers’ Notch State Park, hike in the beautiful Green Mountains, and immerse yourself in the quintessential New England charm of this town.
Continue your road trip by heading to the White Mountains in New Hampshire. Visit the iconic Franconia Notch State Park, hike to the stunning Artists Bluff for panoramic views, and take the scenic Kancamagus Highway, known for its picturesque fall foliage.
As you make your way through New Hampshire, don’t miss a visit to the town of Jackson. Admire the colorful maple trees, take a scenic drive along the Pinkham Notch, and enjoy the stunning fall views of the surrounding White Mountains.
Next, venture to the Berkshires in Massachusetts, a region renowned for its vibrant fall foliage. Visit the charming town of Lenox, explore the picturesque landscapes of the Mount Greylock State Reservation, and indulge in the local farm stands and orchards.
Continue your journey by heading to the vibrant city of Northampton. Explore the charming downtown area, take a leisurely stroll along the Connecticut River, and immerse yourself in the artistic atmosphere of this lively town.
Wrap up your fall foliage road trip with a visit to the town of Salem, Massachusetts. Explore the historic streets, visit the famous Salem Witch Museum, and take a scenic walk along the waterfront to appreciate the fall colors against the backdrop of the ocean.
From Stowe to Salem, this road trip through New England during the fall foliage season will leave you in awe of the vibrant colors and natural beauty that adorns the region. So, pack your camera, hit the road, and get ready for a spectacular display of autumn’s glory in New England.
Road Trip #10: Coastal Delights of Massachusetts and New Hampshire
Embark on a coastal adventure through Massachusetts and New Hampshire as you explore the charming seaside towns, stunning beaches, and scenic landscapes along the coast. From historic landmarks to picturesque shoreline, this road trip will take you through the coastal gems of these two captivating states.
Your journey begins in the historic city of Salem, Massachusetts. Immerse yourself in the rich history of the Salem Witch Trials, explore the vibrant downtown area, and take a stroll along the scenic waterfront.
Next, make your way to the iconic city of Boston. Walk the historic Freedom Trail, visit the USS Constitution Museum, and soak in the lively atmosphere of Faneuil Hall Marketplace.
Continue your road trip by heading to the picturesque town of Newburyport. Explore the charming streets lined with unique shops and restaurants, relax on the sandy shores of Plum Island Beach, and take a scenic boat tour along the Merrimack River.
As you cross into New Hampshire, don’t miss a visit to the vibrant city of Portsmouth. Explore the historic downtown area, take a boat tour along the Piscataqua River, and indulge in fresh seafood at one of the renowned local eateries.
Next, venture to the coastal town of Rye and enjoy the stunning beaches, such as Jenness State Beach and Wallis Sands Beach. Take a walk along the scenic Odiorne Point State Park and soak in the breathtaking views of the Atlantic Ocean.
Continue your coastal exploration by heading north to the town of Hampton. Relax on the popular Hampton Beach, visit the Hampton Beach State Park, and enjoy the lively atmosphere of the boardwalk and arcades.
Wrap up your road trip in the charming town of Portsmouth, New Hampshire. Explore the historic Strawbery Banke Museum, take a scenic walk along Prescott Park, and enjoy a delicious seafood dinner overlooking the waterfront.
From Salem to Portsmouth, this road trip through the coastal delights of Massachusetts and New Hampshire will leave you enamored with the charming seaside towns, stunning beaches, and rich history of these captivating states. So, hit the open road, breathe in the salty air, and embrace the coastal beauty along the way.
Road Trip #11: Historic Eastern Connecticut
Embark on a journey through the historic towns of Eastern Connecticut as you immerse yourself in the rich history, charming architecture, and cultural landmarks of the region. This road trip will take you through the fascinating stories and preserved heritage of Eastern Connecticut.
Your journey begins in the captivating town of Mystic, known for its maritime history and quaint charm. Explore the Mystic Seaport Museum, visit the historic Mystic River drawbridge, and indulge in fresh seafood at one of the local restaurants.
Next, make your way to the town of Stonington, renowned for its preserved colonial architecture and scenic beauty. Take a walk along the picturesque Stonington Borough, visit the historic lighthouse, and appreciate the views of the Atlantic Ocean.
Continue your road trip by heading to the town of Norwich, steeped in history and architectural beauty. Explore the historic Slater Memorial Museum, stroll through the picturesque Yantic Cemetery, and visit the nearby Mohegan Sun Casino for some entertainment.
As you make your way east, don’t miss a visit to the charming town of New London. Walk along the waterfront at Ocean Beach Park, visit the historic United States Coast Guard Academy, and explore the art galleries and shops in downtown New London.
Next, venture to the town of Old Lyme, known for its artistic heritage and scenic beauty. Visit the Florence Griswold Museum, once a gathering place for American Impressionist artists, stroll along the Lyme Street lined with historic homes, and enjoy the serene nature trails in the area.
Wrap up your journey in the historic town of Essex, located along the Connecticut River. Admire the well-preserved colonial buildings, take a leisurely stroll along the charming Main Street, and enjoy a scenic boat ride along the Connecticut River.
From Mystic to Essex, this road trip through historic Eastern Connecticut will transport you back in time as you explore the fascinating stories and preserved heritage of the region. So, hit the road, embrace the captivating history, and delve into the cultural treasures of Eastern Connecticut.
Road Trip #12: Exploring the Lakes of New Hampshire and Maine
Embark on a scenic road trip through the picturesque lakes of New Hampshire and Maine, where tranquility and natural beauty await. This itinerary will take you through charming towns, stunning views, and opportunities for outdoor adventure as you explore the magnificent lakes region.
Your journey begins in the town of Wolfeboro, located on the shores of Lake Winnipesaukee in New Hampshire. Enjoy a scenic boat cruise on the lake, explore the charming downtown area filled with boutiques and restaurants, and hike the trails of the nearby Castle in the Clouds for breathtaking views.
Next, make your way to Lake Winnisquam, one of the smaller yet equally stunning lakes in New Hampshire. Enjoy a relaxing day by the water, go fishing or boating, and savor the peaceful atmosphere that surrounds this hidden gem.
Continue your road trip by heading to the charming town of Meredith, situated on the shores of Lake Winnipesaukee. Explore the shops and art galleries in the downtown area, take a scenic hike up to the Majestic Mount Major for panoramic views, and enjoy a lakefront meal at one of the waterfront restaurants.
As you cross over to Maine and the famous Sebago Lake, be sure to visit the town of Naples. Take a scenic cruise on the Songo River Queen II, explore the Causeway pedestrian bridge, and indulge in some delicious seafood at a waterfront eatery.
Next, venture to Rangeley Lakes in Maine, a region known for its pristine wilderness and stunning lakes. Take a kayak or canoe out on the clear waters, hike the scenic trails of Rangeley Lake State Park, and keep an eye out for wildlife along the way.
Wrap up your journey by visiting Moosehead Lake, the largest lake in Maine. Explore the town of Greenville, take a scenic flight over the lake to admire its vastness, and maybe even spot a moose in the surrounding wilderness.
From Lake Winnipesaukee to Moosehead Lake, this road trip through the lakes of New Hampshire and Maine will immerse you in the serene beauty of the region. So, pack your camera, embrace the tranquility, and get ready for an unforgettable adventure exploring the stunning lakes of New England.
Conclusion
New England is a region filled with captivating landscapes, charming towns, and rich history, making it the perfect destination for an epic road trip. Whether you’re seeking coastal delights, scenic mountain vistas, or a journey through history, New England has it all. From the rugged coastline of Maine to the picturesque lakes of New Hampshire and Vermont’s idyllic charm, each road trip offers a unique and enchanting experience.
As you embark on your New England adventure, be sure to embrace the flexibility and spontaneity that road trips allow. While these itineraries provide a framework, don’t be afraid to venture off the beaten path and discover hidden treasures along the way. Whether it’s stumbling upon a quaint roadside café, witnessing a breathtaking sunset over the mountains, or stumbling upon a charming local festival, some of the best memories are made when we allow ourselves to deviate from the planned route and immerse ourselves in the unexpected.
Remember to take your time and savor the journey. New England is a region best experienced at a leisurely pace, allowing you to soak in the natural beauty, explore charming towns, and interact with the friendly locals. Pack a picnic, stop at scenic overlooks, and take the time to explore the many historic landmarks and cultural attractions that make each destination so special.
Whether you’re a nature enthusiast, history buff, or simply seeking a peaceful getaway, a road trip through New England will not disappoint. Fall in love with the vibrant colors of autumn, breathe in the salty air along the coastline, and embrace the warm hospitality and charm that New England is known for.
So, fuel up your car, grab your camera, and hit the road to create memories that will last a lifetime on an epic road trip through the stunning landscapes, charming towns, and hidden gems of New England.