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The Ultimate New England Fall Road Trip Itinerary


Modified: December 28, 2023

by Daisie Crews



Embarking on a road trip is an exhilarating adventure that allows you to explore new destinations, soak in breathtaking scenery, and create lasting memories. And when it comes to road trips, there’s nothing quite as picturesque and charming as a journey through New England during the fall season.


New England, with its vibrant foliage, quaint towns, and rich history, is a road trip enthusiast’s dream come true. From the bustling streets of Boston to the tranquil landscapes of Vermont, this region offers a diverse range of attractions that will captivate every traveler.


In this ultimate New England fall road trip itinerary, we’ll take you on a journey through some of the region’s most stunning destinations. Whether you’re an outdoor enthusiast, a history buff, or a food lover, this itinerary has something for everyone.


Prepare to be enchanted as we traverse the winding roads and uncover the hidden gems of New England. From the colorful streets of Salem to the majestic peaks of the White Mountains, each day of this itinerary will leave you spellbound.


So grab your map, pack your bags, and let’s hit the road on this unforgettable adventure through New England’s autumn wonderland.


Day 1: Boston, Massachusetts

Begin your New England fall road trip in the vibrant city of Boston, Massachusetts. With its rich history, charming neighborhoods, and thriving food scene, Boston is an ideal starting point for your adventure.


Start your day by exploring the iconic Freedom Trail, a 2.5-mile walking route that takes you through 16 historical sites. From the Massachusetts State House to the Paul Revere House, you’ll be immersed in the city’s colonial past. Don’t forget to stop by Faneuil Hall Marketplace, where you can indulge in delicious local cuisine and shop for unique souvenirs.


In the afternoon, head to Fenway Park, the oldest baseball stadium in the United States. Even if you’re not a sports fan, the atmosphere and history of this iconic venue are worth experiencing. Take a guided tour or catch a game if the season is in full swing.


As the sun sets, make your way to the picturesque waterfront area of the Seaport District. Enjoy a leisurely stroll along the Harborwalk, taking in the stunning skyline views. Treat yourself to a delectable seafood dinner at one of the many renowned waterfront restaurants.


End your day with a visit to the lively neighborhood of Back Bay. Take a walk down Newbury Street, known for its upscale boutiques and charming brownstone buildings. Don’t miss the opportunity to visit the Boston Public Library, a majestic architectural masterpiece.


After a fun-filled day exploring the city, settle into your accommodation for a restful night’s sleep before continuing your New England road trip tomorrow.


Day 2: Salem, Massachusetts

On day 2 of your New England fall road trip, immerse yourself in the enchanting history of Salem, Massachusetts. Known for its infamous witch trials in the late 1600s, Salem offers a unique blend of bewitching attractions and captivating landmarks.


Start your day by visiting the Salem Witch Museum, where you’ll learn about the events that unfolded during the witch trials through a combination of exhibits and presentations. Gain insight into the hysteria that gripped the town during that dark period in history.


Next, take a leisurely stroll through the Salem Maritime National Historic Site, where you can explore the beautifully preserved waterfront district. Visit the Derby Wharf and the Custom House, two significant landmarks that showcase Salem’s maritime heritage.


For lunch, indulge in some local flavors at one of the many charming restaurants in town. Try classic New England dishes like clam chowder or lobster roll, and don’t forget to sample a tasty treat from one of the renowned bakeries for dessert.


In the afternoon, visit the House of the Seven Gables, a historic mansion made famous by Nathaniel Hawthorne’s novel. Take a guided tour of the house and its picturesque gardens, and learn about the inspirations behind the story.


As the day draws to a close, embrace the spooky side of Salem by exploring its eerie attractions. Visit the Salem Witch Trials Memorial, a solemn memorial dedicated to the victims of the trials. Take a guided ghost tour to discover the haunted history of the city.


End your day with a memorable dinner at one of Salem’s atmospheric restaurants, where you can savor delicious cuisine while reflecting on the bewitching experiences of the day.


After a day filled with history, tales of witches, and captivating sights, enjoy a peaceful night’s rest before continuing your New England adventure.


Day 3: Portsmouth, New Hampshire

On day 3 of your New England fall road trip, make your way to the charming coastal town of Portsmouth, New Hampshire. Known for its historic architecture, scenic waterfront, and thriving arts scene, Portsmouth is a delightful destination to explore.


Start your day by taking a stroll along the beautiful waterfront area known as Prescott Park. Admire the colorful gardens, watch boats sail by in the Piscataqua River, and soak in the tranquil atmosphere. If you’re visiting during the fall, you’ll be treated to breathtaking views of the foliage reflecting on the water.


Next, head to Strawbery Banke Museum, a living history museum that gives you a glimpse into Portsmouth’s past. Explore the restored 17th to 19th-century buildings and interact with costumed interpreters who bring the stories of the past to life.


Lunchtime calls for a visit to Market Square, the heart of downtown Portsmouth. This vibrant area is filled with charming shops, art galleries, and local eateries. Treat yourself to a delicious meal at a waterfront restaurant and enjoy the fresh seafood that the region is known for.


In the afternoon, take a tour of the USS Albacore Museum and Park, where you can explore a retired submarine used by the U.S. Navy. Learn about the history of submarine warfare and get a glimpse into the life of a submariner.


For a dose of culture, visit The Music Hall, a historic theater that hosts a variety of performances, from concerts to theatrical productions. Check their schedule to see if there’s a show that piques your interest during your visit.


As the sun sets, head to the Portsmouth Harbor Lighthouse for breathtaking views of the coastline and the Atlantic Ocean. Take a guided tour to learn about the lighthouse’s history and soak in the serene beauty of the surroundings.


End your day with a leisurely dinner at one of Portsmouth’s renowned farm-to-table restaurants, where you can savor delectable dishes made with locally sourced ingredients.


After a day of immersing yourself in Portsmouth’s history, culture, and natural beauty, rest up for the next leg of your New England journey.


Day 4: Portland, Maine

On Day 4 of your New England fall road trip, venture further north to the vibrant city of Portland, Maine. Known for its picturesque coastal landscapes, thriving food scene, and rich maritime history, Portland offers a perfect blend of natural beauty and cultural experiences.


Start your day with a visit to the Portland Head Light, one of the most iconic lighthouses in the United States. Located within Fort Williams Park, this picturesque landmark offers breathtaking views of the rugged coastline. Take a leisurely walk along the cliffside trails and be mesmerized by the crashing waves and panoramic vistas.


After immersing yourself in the coastal beauty, head to the historic Old Port district. This charming area is filled with cobblestone streets, boutique shops, and art galleries. Explore the unique boutiques, visit local artisans, and indulge in a delicious brunch at one of the many acclaimed restaurants.


Next, take a scenic cruise to Casco Bay to discover the enchanting islands that dot the coast. Enjoy the fresh sea breeze as you sail by lighthouses, rocky shores, and picturesque fishing villages. Keep an eye out for local wildlife, including seals and seabirds.


No visit to Portland would be complete without delving into its world-renowned food scene. Sample fresh seafood dishes at the vibrant Portland Public Market or visit the acclaimed restaurants that offer everything from lobster rolls to farm-to-table cuisine.


In the afternoon, dive into the city’s rich maritime history at the Maine Maritime Museum. This comprehensive museum showcases exhibits on shipbuilding, lobstering, and marine artifacts. Take a guided tour or explore at your own pace to learn about Maine’s seafaring heritage.


As the day winds down, make your way to the Eastern Promenade, a waterfront park offering stunning views of Casco Bay. Take a leisurely stroll along the trails, have a picnic on the grassy fields, or simply relax and enjoy the mesmerizing sunset.


End your day in Portland with a visit to one of the local breweries or distilleries, where you can sample craft beers or spirits made with Maine’s finest ingredients.


After a day of immersing yourself in Portland’s coastal beauty and culinary delights, find comfort in your accommodations and prepare for the next chapter of your New England road trip.


Day 5: Acadia National Park, Maine

Prepare to be awe-inspired as you spend the fifth day of your New England fall road trip in the breathtaking natural splendor of Acadia National Park. Located along the rugged coast of Maine, Acadia National Park offers stunning landscapes, scenic hiking trails, and panoramic views that will leave you speechless.


Start your day early and make your way to the summit of Cadillac Mountain, the highest point on the eastern seaboard. Arriving at sunrise will reward you with a mesmerizing display of colors as the sun paints the sky and illuminates the islands below. Capture the moment and revel in the serenity of this stunning vantage point.


After witnessing the beauty of sunrise, explore the park’s extensive network of hiking trails. Choose from a variety of options that cater to different fitness levels and interests. Whether you’re looking for a leisurely stroll along the shoreline or a challenging hike up a mountain, Acadia has trails to suit every adventurer.


For lunch, enjoy a picnic amidst the gorgeous surroundings or head to the nearby town of Bar Harbor to savor delicious seafood at one of the local eateries.


In the afternoon, embark on a scenic drive along the Park Loop Road, a winding road that showcases the park’s natural wonders. Stop at iconic landmarks such as Thunder Hole, where the crashing waves create a thunderous sound, and Jordan Pond, with its serene waters and picturesque views.


As the day progresses, make your way to the Bass Harbor Head Lighthouse, a picturesque landmark perched on the rocky shoreline. Capture postcard-worthy photos and marvel at the rugged beauty of the surrounding landscape.


Before leaving the park, don’t miss the opportunity to take a leisurely bike ride along the Carriage Roads. These historic pathways, built by John D. Rockefeller Jr., wind through beautiful forests and offer a unique way to explore the park’s inner reaches.


As the sun sets over Acadia, relish in the natural beauty surrounding you and reflect on the unforgettable experiences of the day. Head back to your accommodation feeling refreshed and grateful for the wonders nature has to offer.


Day 6: White Mountains, New Hampshire

On the sixth day of your New England fall road trip, venture into the majestic White Mountains of New Hampshire. Known for their stunning beauty, endless outdoor activities, and charming small towns, the White Mountains offer a perfect blend of adventure and relaxation.


Start your day by visiting Franconia Notch State Park, home to some of the most iconic landmarks in the region. Take a scenic drive through the park, making stops at popular attractions like the Flume Gorge and the Basin, where you can marvel at the natural wonders created by glacial erosion.


Continue your exploration by hopping on the Cannon Mountain Aerial Tramway, which will take you to the summit of Cannon Mountain. Enjoy breathtaking vistas of the surrounding peaks and valleys as you ascend. If you’re feeling adventurous, embark on one of the hiking trails that originate from the summit.


For lunch, visit one of the charming small towns in the area, such as North Conway or Lincoln. These towns are known for their cozy cafes, family-owned restaurants, and unique boutique shops.


In the afternoon, immerse yourself in the beauty of the White Mountains by embarking on a scenic hike. With a variety of trails available, choose one that matches your desired level of difficulty and offers stunning views of the surrounding landscape. Whether you opt for a leisurely walk around a peaceful lake or a challenging climb to a mountain summit, you’ll be rewarded with breathtaking fall foliage and panoramic vistas.


As the day winds down, make your way to the Mount Washington Cog Railway, the world’s first mountain-climbing cog railway. Take a ride to the summit of Mount Washington, the tallest peak in the Northeast, and be amazed by the expansive views from the top.


End your day in the White Mountains by enjoying a hearty dinner at a local restaurant, where you can savor comfort food and warm beverages. Reflect on the day’s adventures and bask in the peaceful ambiance of this magnificent mountain range.


After a day of immersing yourself in the natural wonders of the White Mountains, return to your accommodation and prepare for another day of exploration tomorrow.


Day 7: Stowe, Vermont

Welcome to Stowe, Vermont – a charming town nestled in the heart of the Green Mountains. On the seventh day of your New England fall road trip, prepare to be enchanted by the picturesque landscapes, outdoor activities, and vibrant local culture that Stowe has to offer.


Start your day in Stowe Village, where you can explore the quaint streets lined with unique shops, art galleries, and cozy cafes. Browse through the locally-made crafts and artisanal products, and perhaps take a moment to indulge in a freshly brewed cup of Vermont’s famous maple syrup.


Next, head out into the great outdoors and immerse yourself in Stowe’s natural beauty. Visit the iconic Smugglers’ Notch State Park, known for its breathtaking hiking trails, cascading waterfalls, and stunning viewpoints. Choose a trail that suits your preferences, and embark on an adventure through the wooded wonderland.


Lunchtime calls for a visit to one of the local breweries or cider houses, where you can sample some of Vermont’s finest craft beers and ciders. Pair your beverage with a delicious farm-to-table meal and savor the flavors of the region.


In the afternoon, make your way to Mount Mansfield, the highest peak in Vermont. Take the Stowe Mountain Resort Gondola for a scenic ride to the summit, where you’ll be treated to breathtaking panoramic views of the surrounding mountains and valleys. If you’re feeling adventurous, explore the hiking trails that wind through the area.


As the day draws to a close, consider a visit to the Trapp Family Lodge, where the famous von Trapp family (of The Sound of Music fame) made their home. Take a guided tour of the property, stroll through the beautiful gardens, and enjoy a traditional Austrian dinner at the lodge’s renowned restaurant.


End your day in Stowe by indulging in some stargazing. With its relatively low light pollution, the area provides a perfect setting for observing the night sky. Find a cozy spot in nature, lie back, and let yourself be awe-struck by the brilliance of the stars.


After a day of exploring the charming town of Stowe and immersing yourself in its natural wonders, find comfort in your accommodation and rest up for the next leg of your New England adventure.


Day 8: Manchester, Vermont

On the eighth day of your New England fall road trip, venture to the quaint town of Manchester, Vermont. Known for its picturesque landscapes, charming shops, and rich history, Manchester offers a delightful blend of outdoor activities and small-town charm.


Start your day by exploring the Equinox Preserve, a pristine nature reserve with miles of scenic trails. Take a leisurely hike through the colorful forest, soak in the peaceful ambiance, and be on the lookout for native wildlife.


After working up an appetite, head to the heart of Manchester Village and enjoy a leisurely brunch at one of the renowned local eateries. Indulge in Vermont classics like maple syrup-drizzled pancakes or farm-fresh eggs while taking in the enchanting surroundings.


In the afternoon, discover the rich history of Manchester at the Hildene Estate. This stunning property was once the summer home of Robert Todd Lincoln, son of President Abraham Lincoln. Take a guided tour of the mansion, explore the beautifully manicured gardens, and learn about the Lincoln family’s legacy.


For some retail therapy, visit the Manchester Designer Outlets. This premier shopping destination offers a wide array of high-end brands at discounted prices. Shop for clothing, accessories, and home goods, and score some great deals on luxury items.


As the day progresses, make your way to the iconic covered bridges that dot the countryside. These charming structures are not only picturesque but also offer a glimpse into Vermont’s history and identity.


End your day by enjoying a delicious dinner at one of Manchester’s farm-to-table restaurants, where you can indulge in fresh, locally sourced cuisine. Raise a glass of Vermont craft beer or wine to toast the flavors of the region.


After a day of exploring Manchester’s natural beauty, immersing yourself in its history, and experiencing the charm of the town, find rest and relaxation in your accommodation, preparing for the next chapter of your New England adventure.


Day 9: Berkshires, Massachusetts

On the ninth day of your New England fall road trip, venture to the picturesque region of the Berkshires in Massachusetts. Known for its stunning landscapes, cultural attractions, and charming towns, the Berkshires offer a perfect blend of outdoor adventures and artistic experiences.


Begin your day by exploring the natural beauty of the area at Mount Greylock State Reservation. This expansive park is home to the highest peak in Massachusetts, Mount Greylock. Embark on a scenic hike to the summit, where you’ll be rewarded with panoramic views of the surrounding mountains and forests.


After your hike, make your way to the Massachusetts Museum of Contemporary Art (MASS MoCA) in North Adams. This renowned museum is housed in a former textile mill and showcases a diverse range of contemporary art exhibitions. Explore the vast galleries and immerse yourself in artistic expressions.


For lunch, visit one of the quaint towns in the Berkshires, such as Lenox or Stockbridge. These charming communities offer a variety of culinary delights, from cozy cafes and farm-to-table restaurants to local bakeries serving delectable treats.


In the afternoon, indulge in the area’s rich cultural scene by visiting Tanglewood, the summer home of the Boston Symphony Orchestra. Take a guided tour of the grounds and enjoy a concert if there are performances happening during your visit. If not, simply bask in the serenity of the beautiful landscape.


As the day winds down, discover the literary history of the Berkshires at The Mount, the former home of American author Edith Wharton. Explore the stunning gardens, tour the historic house, and learn about Wharton’s influential contributions to literature.


End your day with a relaxing dinner at one of the charming restaurants in the Berkshires, where you can savor locally sourced ingredients and exquisite flavors. Reflect on the natural beauty and cultural richness of the region as you enjoy a delightful meal.


After a day spent immersing yourself in the artistic and natural wonders of the Berkshires, find comfort and rejuvenation in your accommodation, preparing for the final day of your unforgettable New England road trip.


Day 10: Newport, Rhode Island

On the final day of your New England fall road trip, make your way to the charming coastal city of Newport, Rhode Island. Known for its opulent mansions, stunning beaches, and rich maritime history, Newport offers a captivating blend of beauty and elegance.


Start your day by exploring the famous Newport Cliff Walk, a 3.5-mile scenic trail that winds along the coastline. Take in breathtaking views of the Atlantic Ocean on one side and admire the grandeur of Newport’s historic mansions on the other. Marvel at the Gilded Age architecture and imagine what life was like for the wealthy elite of the time.


After your walk, head to the International Tennis Hall of Fame, located in the heart of Newport. Take a guided tour of the museum and learn about the history of tennis, see memorabilia from legendary players, and even try your hand at some interactive exhibits.


For lunch, enjoy some fresh seafood at one of Newport’s waterfront restaurants. Indulge in a lobster roll or sample the local catch of the day while taking in the scenic views of the harbor.


In the afternoon, visit one of Newport’s iconic mansions, such as The Breakers or Marble House. These lavish properties were once the summer homes of wealthy families and offer a glimpse into the luxurious lifestyle of the Gilded Age. Take a guided tour and marvel at the intricate architectural details, opulent furnishings, and expansive gardens.


As the day progresses, make your way to Newport’s stunning beaches. Whether you choose Easton’s Beach (also known as First Beach) or Sachuest Beach (also known as Second Beach), you’ll be treated to pristine sandy shores and refreshing ocean waters. Take a leisurely walk along the coastline, soak up the sun, or dip your toes in the water.


End your day with a picturesque sunset cruise along Newport Harbor. Relax on board as you sail past breathtaking waterfront estates and enjoy the beautiful colors of the setting sun reflecting on the water.


After a day filled with history, elegance, and natural beauty, find a local restaurant to enjoy a delicious dinner. Raise a glass to a successful and memorable New England fall road trip and savor the last moments of your journey in Newport.


As your New England adventure comes to a close, take a moment to reflect on the incredible experiences, scenic landscapes, and vibrant culture you’ve encountered along the way. Cherish the memories made, and perhaps start planning your next road trip to explore even more of the wonders that the world has to offer.



As your New England fall road trip comes to an end, you can reflect on the incredible journey you’ve embarked upon. From the bustling streets of Boston to the charming coastal towns of Maine, and from the majestic peaks of the White Mountains to the opulent mansions of Newport, you’ve experienced the diverse beauty and rich history of this captivating region.


New England during the fall season is truly a sight to behold. The vibrant foliage, picturesque landscapes, and warm hospitality of the locals create an enchanting atmosphere that is unmatched. Whether you immersed yourself in the history of Salem, hiked the pristine trails of Acadia National Park, or indulged in culinary delights from quaint towns along the way, each day brought new adventures and unforgettable memories.


Throughout your journey, you’ve witnessed the breathtaking beauty of nature, explored historic sites, sampled diverse cuisine, and connected with the local culture. Each destination offered its own unique charm and allowed you to fully immerse yourself in the essence of New England.


As you reflect on the sights, flavors, and experiences of your New England fall road trip, you may find yourself longing to return to this region again. The beauty of New England, with its ever-changing seasons and timeless charm, will continue to beckon travelers to explore its wonders.


So, whether you’re an outdoor enthusiast, a history buff, or a lover of quaint towns and scenic landscapes, a road trip through New England during the fall season is an absolute must. With its vibrant colors, rich history, and warm hospitality, this region offers a journey that will leave you with memories to last a lifetime.


Remember, the open road is waiting, and New England is ready to welcome you on your next adventure. So pack your bags, hit the road, and let the beauty of New England’s fall foliage unfold before your eyes.