The Ultimate New England Road Trip Itinerary

Introduction

Embarking on a road trip is one of the best ways to explore the scenic beauty and rich history of New England. From charming coastal towns to picturesque mountainscapes, New England offers a diverse range of experiences for travelers seeking adventure, relaxation, and cultural immersion.

This ultimate New England road trip itinerary will take you through some of the region’s most iconic destinations, allowing you to soak in the beauty of each stop and create unforgettable memories along the way.

Spanning 14 days, this itinerary will guide you through Massachusetts, Rhode Island, Connecticut, Maine, New Hampshire, and Vermont. Each day will introduce you to unique attractions, historical sites, and local flavors, ensuring a well-rounded exploration of New England’s hidden gems.

Whether you’re a history buff, nature lover, or food enthusiast, this road trip itinerary has something for everyone. So buckle up, hit the road, and prepare for an incredible journey through the heart of New England.

Important Note: It’s always a good idea to check for any travel restrictions, park closures, or necessary reservations before embarking on your road trip. Be sure to review the latest guidelines and recommendations from relevant authorities to ensure a safe and enjoyable adventure.

Day 1: Boston

Your New England road trip begins in the vibrant city of Boston. Start your day with a visit to the historic Freedom Trail, a 2.5-mile trail that takes you through 16 significant sites related to the American Revolution. Immerse yourself in the rich history of Boston as you explore landmarks like the Massachusetts State House, Paul Revere’s House, and the Old North Church.

After a morning of history, treat yourself to a delicious seafood lunch at one of the city’s renowned seafood restaurants. Indulge in fresh lobster rolls, clam chowder, or New England-style fried clams.

In the afternoon, head to the picturesque waterfront neighborhood of Charlestown and take a ferry to the iconic Boston Harbor Islands. Explore the natural beauty and hiking trails of the islands, or simply relax and enjoy the stunning views of the city skyline.

As the evening approaches, make your way to Fenway Park, one of the oldest and most beloved baseball stadiums in the country. Catch a Red Sox game if it’s baseball season, or take a guided tour to learn about the history of this iconic venue.

End your day with a stroll through the lively streets of the historic North End. Known as Boston’s Little Italy, this neighborhood is filled with Italian bakeries, restaurants, and cafes. Treat yourself to a delicious cannoli or gelato before calling it a night.

Accommodation Recommendation: The Liberty Hotel, located in the historic Beacon Hill neighborhood, offers luxurious accommodations with a touch of history.

Key Attractions: Freedom Trail, Boston Harbor Islands, Fenway Park, North End.

Pro Tip: Consider purchasing a Go Boston Pass, which provides discounted admission to multiple attractions and can help you save money during your time in Boston.

Day 2: Cape Cod

On day 2 of your New England road trip, venture south of Boston to the picturesque Cape Cod peninsula. Known for its pristine beaches, quaint villages, and charming lighthouses, Cape Cod offers a perfect escape from the city.

Start your day with a visit to the Cape Cod National Seashore, a stunning stretch of coastline with sandy dunes and rolling waves. Take a leisurely stroll along the beach, or if you’re feeling adventurous, rent a bicycle and explore the Cape Cod Rail Trail, a scenic path that winds through the picturesque towns of Cape Cod.

In the afternoon, head to the charming town of Provincetown, located at the tip of Cape Cod. Known for its vibrant art scene and welcoming LGBTQ+ community, Provincetown offers a unique and eclectic atmosphere. Explore the town’s art galleries, boutique shops, and vibrant cafes, and be sure to visit the iconic Pilgrim Monument for a panoramic view of the surrounding area.

No trip to Cape Cod is complete without indulging in some delicious seafood. Make sure to stop by one of the local seafood shacks for some fresh fried clams, lobster rolls, or clam chowder.

As the day comes to an end, catch a stunning Cape Cod sunset at one of the many beautiful beaches along the coast. Relax on the sand, listen to the sound of the waves, and take in the natural beauty that Cape Cod has to offer.

Accommodation Recommendation: The Chatham Bars Inn, located in the charming town of Chatham, offers luxurious accommodations and stunning ocean views.

Key Attractions: Cape Cod National Seashore, Cape Cod Rail Trail, Provincetown, Pilgrim Monument.

Pro Tip: Consider taking a whale-watching cruise from Provincetown to catch a glimpse of majestic humpback whales and other marine wildlife in their natural habitat.

Day 3: Martha’s Vineyard

On day 3 of your New England road trip, hop aboard a ferry and set sail for the beautiful island of Martha’s Vineyard. Known for its pristine beaches, charming towns, and laid-back atmosphere, Martha’s Vineyard is a must-visit destination for nature lovers and relaxation seekers.

Start your day by exploring the idyllic town of Edgartown, known for its beautifully preserved 19th-century architecture and picturesque harbor. Stroll along Main Street, lined with boutique shops and art galleries, and take in the charming New England vibe.

Next, head to the breathtaking South Beach, a long stretch of sandy shores and rolling waves. Take a dip in the refreshing waters, relax on the beach with a good book, or try your hand at surfing or paddleboarding.

In the afternoon, make your way to the colorful town of Oak Bluffs, famous for its Victorian-style gingerbread cottages. Explore the whimsical streets lined with these unique cottages, and be sure to visit the iconic Flying Horses Carousel, the oldest operating carousel in the United States.

For a taste of the island’s culinary delights, indulge in fresh seafood at one of the many waterfront restaurants. From locally caught lobster and oysters to traditional New England clam bakes, Martha’s Vineyard offers a wide range of delectable dishes.

As the day comes to a close, catch a stunning sunset at one of the island’s scenic spots. Either relax on one of the many beautiful beaches or head to Gay Head Cliffs in Aquinnah for a dramatic view of the cliffs against the backdrop of the setting sun.

Accommodation Recommendation: The Harbor View Hotel in Edgartown offers elegant accommodations with breathtaking water views.

Key Attractions: Edgartown, South Beach, Oak Bluffs, Flying Horses Carousel, Aquinnah Cliffs.

Pro Tip: Rent a bike to explore Martha’s Vineyard at your own pace. The island offers bike-friendly paths that allow you to discover its natural beauty and charming towns with ease.

Day 4: Newport, Rhode Island

On day 4 of your New England road trip, make your way to the elegant seaside town of Newport, Rhode Island. Known for its opulent mansions, stunning coastal scenery, and rich maritime history, Newport offers a blend of charm and luxury.

Start your day with a visit to the renowned Newport Mansions, a collection of historic mansions that once belonged to wealthy New York families. Take a guided tour of The Breakers, Marble House, or The Elms, and marvel at the grandeur and intricate architecture of these Gilded Age gems.

After exploring the mansions, head to the stunning Cliff Walk, a scenic pathway that hugs the coastline and offers panoramic views of the ocean and the mansions. Take a leisurely stroll along the path, enjoy the fresh sea breeze, and be in awe of the natural beauty that surrounds you.

In the afternoon, visit the historic Newport Harbor and take a sailing cruise to experience the city from a different perspective. Enjoy the gentle rocking of the boat as you sail past charming lighthouses, picturesque islands, and luxurious yachts.

Newport is also known for its vibrant dining scene. Treat yourself to a delicious seafood feast at one of the waterfront restaurants, where you can savor fresh local catches like lobster, clams, and oysters.

End your day with a visit to the International Tennis Hall of Fame, located in the heart of Newport. Explore the museum, learn about the history of tennis, and even try your hand at a game on one of the grass courts.

Accommodation Recommendation: The Chanler at Cliff Walk offers luxurious rooms with stunning views of the ocean and easy access to the Newport Mansions.

Key Attractions: Newport Mansions, Cliff Walk, Newport Harbor, International Tennis Hall of Fame.

Pro Tip: Consider taking a harbor cruise at sunset to witness the breathtaking colors as the sun dips below the horizon, casting a golden glow on the waterfront and mansions.

Day 5: Mystic, Connecticut

On day 5 of your New England road trip, venture to the charming coastal town of Mystic, Connecticut. Known for its maritime history, charming village atmosphere, and delicious seafood, Mystic offers a delightful mix of attractions for all types of travelers.

Start your day by visiting the Mystic Seaport Museum, the nation’s leading maritime museum. Immerse yourself in the history of seafaring as you explore historic ships, exhibits, and interactive displays. Learn about the art of shipbuilding, discover the lives of sailors, and even set sail on a historic vessel if available.

Next, stroll along the scenic Mystic River and explore the Mystic Village, a picturesque shopping destination filled with boutique stores, galleries, and restaurants. Indulge in a classic New England seafood lunch at one of the waterfront restaurants, where you can enjoy fresh catches like clam chowder, lobster rolls, and fried clams.

In the afternoon, visit the Mystic Aquarium, where you can encounter a variety of marine life, including beluga whales, sea turtles, and penguins. Watch captivating shows and interactive exhibits that educate and entertain visitors of all ages.

For a unique experience, take a cruise on a historic wooden schooner along the coast, or rent a kayak and explore Mystic’s waterways at your own pace. Enjoy scenic views, spot wildlife, and feel the tranquility of being out on the water.

As the day winds down, head to downtown Mystic to sample some of the local flavors. Visit a brewery or distillery to taste craft beers or spirits made with locally sourced ingredients. Afterwards, stroll along the charming streets and browse through the artisan shops and galleries that showcase the talents of local artists and craftsmen.

Accommodation Recommendation: The Whaler’s Inn, located in the heart of Mystic, offers comfortable accommodations with a touch of New England charm.

Key Attractions: Mystic Seaport Museum, Mystic Village, Mystic Aquarium, Mystic River.

Pro Tip: Try the famous Mystic Pizza, made famous by the 1988 movie. This local landmark offers delicious pizza with a variety of toppings to satisfy any craving.

Day 6: Providence, Rhode Island

On day 6 of your New England road trip, make your way to the charming and vibrant city of Providence, Rhode Island. Known for its rich history, diverse culinary scene, and thriving arts community, Providence offers a unique blend of old-world charm and modern attractions.

Start your day by exploring the picturesque Waterplace Park, a beautifully landscaped park located along the Providence River. Take a leisurely stroll along the riverwalk, enjoy the sight of the iconic WaterFire installation if it’s scheduled, and take in the scenic views of the city’s skyline.

Next, make your way to the Rhode Island State House, an impressive marble building that houses the state’s government. Take a guided tour to learn about the history of the building and admire the stunning architecture and artwork.

In the afternoon, visit the historic Federal Hill neighborhood, also known as “Little Italy.” Explore the streets lined with Italian restaurants, bakeries, and specialty shops. Indulge in a traditional Italian meal, sample some mouthwatering pastries, and soak in the lively atmosphere of this vibrant neighborhood.

Afterward, venture to the RISD Museum, part of the Rhode Island School of Design. Discover an impressive collection of artworks from various periods and cultures, including ancient Egyptian artifacts, European paintings, contemporary pieces, and much more.

To end your day, explore the DownCity area, the heart of Providence’s downtown. Browse through the eclectic mix of shops, boutiques, and galleries, and grab a delicious dinner at one of the many restaurants offering diverse cuisine options.

Accommodation Recommendation: The Dean Hotel, located in DownCity, offers stylish and comfortable accommodations in the heart of Providence.

Key Attractions: Waterplace Park, Rhode Island State House, Federal Hill, RISD Museum, DownCity.

Pro Tip: Take a canal tour to explore the city from a different perspective. These relaxing boat tours provide interesting insights into Providence’s history while giving you a unique view of its architecture and landmarks.

Day 7: Portland, Maine

On day 7 of your New England road trip, venture to the vibrant and charming city of Portland, Maine. Known for its picturesque waterfront, thriving food scene, and rich maritime history, Portland offers a delightful mix of cultural attractions and natural beauty.

Start your day by exploring the historic Old Port district, a bustling waterfront area filled with cobblestone streets, boutique shops, and waterfront restaurants. Take a leisurely stroll along the harbor, browse through the unique shops, and soak in the maritime atmosphere.

Next, visit the Portland Head Light, one of the oldest lighthouses in the United States. Located in Fort Williams Park, this iconic landmark offers breathtaking views of the rugged coastline and the Atlantic Ocean. Explore the surrounding park, have a picnic with scenic views, and capture memorable photos of the lighthouse.

Journey over to the Portland Museum of Art, where you can admire a vast collection of artwork from different periods and cultures. The museum showcases works by renowned artists such as Winslow Homer and Andrew Wyeth, as well as contemporary exhibits that highlight local and emerging artists.

In the afternoon, satisfy your taste buds with a visit to the famous Portland Lobster Company or one of the many local seafood restaurants. Indulge in a classic Maine lobster roll or feast on freshly caught seafood delicacies.

Afterward, take a relaxing stroll through the historic Western Promenade, a park that offers panoramic views of the city and the Fore River. Enjoy the lush green surroundings, take in the fresh sea air, and unwind in this tranquil setting.

As the day comes to an end, explore the vibrant arts district of Portland. Visit art galleries, catch a show at one of the theaters, or relax at a local brewery or distillery. Enjoy the creative energy and eclectic atmosphere that makes Portland a hub for artists and artisans.

Accommodation Recommendation: The Press Hotel, located in the heart of downtown Portland, offers luxurious accommodations in a historic building with a modern touch.

Key Attractions: Old Port, Portland Head Light, Portland Museum of Art, Western Promenade, Arts District.

Pro Tip: Don’t leave Portland without tasting some of the local craft beers. The city is known for its thriving microbrewery scene, so make sure to try a few unique and flavorful brews.

Day 8: Acadia National Park

On day 8 of your New England road trip, immerse yourself in the natural wonders of Acadia National Park. Located on Mount Desert Island in Maine, Acadia National Park is a paradise of rugged coastline, pristine lakes, and majestic mountains.

Start your day by driving along the Park Loop Road, a scenic route that takes you through the highlights of the park. Stop at the Jordan Pond House, nestled next to a beautiful pond, and enjoy a traditional Maine popover and tea while taking in the stunning views.

Next, head to the summit of Cadillac Mountain, the highest point on the east coast of the United States. Enjoy breathtaking panoramic views of the surrounding islands, ocean, and mountains. If you’re an early riser, consider catching the sunrise from Cadillac Mountain, as it is one of the first places in the country to see the sun rise.

Continue your exploration by taking a hike on one of the many scenic trails in the park. The Precipice Trail offers a thrilling ascent up the rocky cliffs, while the Jordan Pond Path provides a more leisurely stroll along the shoreline. Choose a trail that suits your fitness level and enjoy the beauty of Acadia’s diverse landscapes.

For a unique perspective of the park, take a scenic drive along the Park Loop Road to reach the beautiful Sand Beach. Take a refreshing dip in the ocean or simply relax on the sandy shores, surrounded by the rugged cliffs and stunning coastal scenery.

In the afternoon, visit the charming town of Bar Harbor, located just outside the park. Explore the bustling streets lined with shops, galleries, and restaurants. Enjoy a delicious seafood dinner at one of the waterfront eateries and sample some of Maine’s famous blueberry pie.

As the day comes to a close, head back to the park to catch a stunning sunset at Schoodic Point. Offering unobstructed views of the rocky coastline and crashing waves, Schoodic Point is the perfect spot to witness nature’s evening spectacle.

Accommodation Recommendation: The Bar Harbor Inn and Spa offers comfortable accommodations with beautiful ocean views and easy access to both the park and the town of Bar Harbor.

Key Attractions: Park Loop Road, Jordan Pond House, Cadillac Mountain, Precipice Trail, Sand Beach, Schoodic Point.

Pro Tip: Consider visiting during the fall season when the foliage transforms the landscapes into a vibrant mix of red, orange, and gold. The park is truly a sight to behold during this time of year.

Day 9: Kennebunkport and Ogunquit

On day 9 of your New England road trip, explore the charming coastal towns of Kennebunkport and Ogunquit in Maine. These picturesque destinations offer breathtaking beaches, scenic views, and a relaxed seaside atmosphere.

Start your day by driving to Kennebunkport, a quintessential New England town known for its rich colonial history and stunning coastal beauty. Take a leisurely walk through Dock Square, the heart of the town, and browse through the boutique shops and art galleries that line the streets.

Next, visit the iconic Bush compound, the summer retreat of the Bush family. Take a guided trolley tour to learn about the history of the compound and its connection to American politics. Don’t forget to snap a photo at the scenic lookout at Walker’s Point, which offers stunning views of the Atlantic Ocean.

Indulge in a delicious seafood lunch at one of the local seafood shacks or waterfront restaurants. Feast on fresh lobster, clams, or shrimp while enjoying the coastal breeze and panoramic views.

Afterward, make your way to the charming town of Ogunquit, famous for its beautiful sandy beaches and dramatic rocky cliffs. Spend the afternoon on Ogunquit Beach, where you can relax on the soft sand, swim in the refreshing ocean waters, or take a leisurely stroll along Marginal Way, a scenic cliffside trail that offers breathtaking views of the coast.

For a unique experience, visit the Ogunquit Museum of American Art, which showcases a collection of American art from the late 19th century to the present. Explore the museum’s exhibitions, including paintings, sculptures, and photography, and immerse yourself in the beauty of American creativity.

As the day winds down, head to Perkins Cove, a charming harbor village in Ogunquit. Explore the local shops, grab an ice cream cone, and admire the fishing boats as they come and go. Consider taking a scenic boat tour to experience the beauty of the coastline from the water.

Accommodation Recommendation: The Nonantum Resort in Kennebunkport offers comfortable accommodations with coastal charm and easy access to the town’s attractions.

Key Attractions: Dock Square, Bush compound, Ogunquit Beach, Marginal Way, Ogunquit Museum of American Art, Perkins Cove.

Pro Tip: Don’t miss the opportunity to try a classic Maine lobster roll. Kennebunkport and Ogunquit are renowned for their delicious lobster dishes, and indulging in a freshly caught lobster roll is a must-do experience.

Day 10: Portsmouth, New Hampshire

On day 10 of your New England road trip, venture to the charming city of Portsmouth, New Hampshire. Located on the picturesque Piscataqua River, Portsmouth offers a delightful blend of history, culture, and scenic beauty.

Start your day by exploring downtown Portsmouth’s historic Market Square. Stroll through the cobblestone streets, admire the beautifully preserved Georgian architecture, and visit the boutique shops, art galleries, and charming cafes that line the area.

Next, take a guided tour of the Strawbery Banke Museum, an outdoor history museum that showcases over 400 years of New England history through restored homes, exhibits, and costumed interpreters. Immerse yourself in the stories of the past as you explore the living history museum.

Afterward, visit the picturesque Prescott Park, located along the riverfront. Enjoy a relaxing walk through the park’s gardens, take in the panoramic views of the harbor, and, if timing permits, catch a live performance at the park’s outdoor theater.

For lunch, indulge in some of Portsmouth’s culinary delights. The city is known for its vibrant food scene, from fresh seafood to farm-to-table cuisine. Try a classic New England clam chowder or savor delicious lobster dishes at one of the waterfront restaurants.

In the afternoon, explore the USS Albacore Museum and Park, where you can step aboard a retired U.S. Navy submarine and learn about its history and significance. Discover the inner workings of a submarine and gain insight into the life of submariners.

As the day comes to a close, head to the picturesque coastal town of New Castle, located just a short drive from Portsmouth. Explore the historic Wentworth by the Sea Hotel, stroll through the charming neighborhoods, and enjoy the stunning views of the ocean and neighboring islands.

Accommodation Recommendation: The Hotel Portsmouth offers stylish and comfortable accommodations in the heart of downtown Portsmouth, within walking distance of the city’s main attractions.

Key Attractions: Market Square, Strawbery Banke Museum, Prescott Park, USS Albacore Museum and Park, New Castle.

Pro Tip: Take a scenic harbor cruise or rent a kayak to explore the Piscataqua River and admire Portsmouth from the water. This allows you to experience the city’s coastal beauty from a unique perspective.

Day 11: White Mountains, New Hampshire

On day 11 of your New England road trip, venture into the breathtaking landscapes of the White Mountains in New Hampshire. Known for their rugged beauty, stunning peaks, and outdoor recreational opportunities, the White Mountains offer an unforgettable natural getaway.

Start your day by driving along the scenic Kancamagus Highway, a 34.5-mile road that meanders through the heart of the White Mountains. Enjoy the panoramic views of forests, rivers, and mountains as you wind your way through this scenic byway. Make sure to stop at picturesque overlooks and take in the stunning vistas.

Next, visit the iconic Mount Washington, the highest peak in the Northeastern United States. Take a scenic drive up the Mount Washington Auto Road or hop aboard the Mount Washington Cog Railway for a unique and thrilling ascent to the summit. Enjoy breathtaking views of the surrounding mountains and valleys from the observation deck at the top.

In the afternoon, explore the beautiful Franconia Notch State Park, nestled in the heart of the White Mountains. Take a leisurely hike along the well-maintained trails that lead to stunning waterfalls, such as the popular Flume Gorge or the scenic Arethusa Falls. Enjoy the tranquility of the forest and marvel at the natural beauty that surrounds you.

For a scenic adventure, take a ride on the Cannon Mountain Aerial Tramway, which offers panoramic views of the White Mountains and the surrounding area. At the summit, you can explore observation decks, visit the New England Ski Museum, or take a leisurely hike along the trails.

As the day comes to a close, head to the charming town of North Conway, known for its shopping outlets and outdoor activities. Explore the quaint downtown area, browse through the unique shops, and enjoy a delicious meal at one of the local restaurants.

Accommodation Recommendation: The Omni Mount Washington Resort, located in Bretton Woods, offers luxurious accommodations with stunning views of the surrounding mountains.

Key Attractions: Kancamagus Highway, Mount Washington, Franconia Notch State Park, Flume Gorge, Cannon Mountain Aerial Tramway, North Conway.

Pro Tip: Check the weather conditions and come prepared with appropriate clothing and gear, especially if you plan on hiking or visiting the higher elevations. The weather in the White Mountains can be unpredictable, so it’s always best to be prepared.

Day 12: Burlington, Vermont

On day 12 of your New England road trip, visit the vibrant city of Burlington, Vermont. Situated on the shores of Lake Champlain and surrounded by the scenic Green Mountains, Burlington offers a unique blend of natural beauty, cultural attractions, and a laid-back atmosphere.

Start your day by exploring the charming Church Street Marketplace, a pedestrian-only street filled with boutique shops, restaurants, and cafes. Stroll along the cobblestone streets, soak in the lively atmosphere, and enjoy the live street performances that often take place.

Next, take a leisurely walk or bike ride along the scenic Burlington Bike Path, which hugs the shoreline of Lake Champlain. Enjoy the panoramic views of the lake and the Adirondack Mountains as you breathe in the fresh mountain air.

In the afternoon, visit the vibrant ArtsRiot Food Truck Stop, a gathering spot for local food trucks offering a variety of delicious cuisine. Sample unique dishes made with local ingredients while enjoying live music and a vibrant community atmosphere.

Continue your exploration at the Shelburne Museum, located just outside Burlington. This unique museum showcases American folk art, paintings, sculptures, and historic buildings spread across 45 acres. Explore the beautifully landscaped grounds and immerse yourself in the rich history and culture of the region.

For a taste of Vermont’s renowned craft beer scene, visit one of the local breweries in Burlington. Take a guided tour, learn about the brewing process, and sample a variety of delicious brews.

As the day winds down, head to the Waterfront Park, a scenic waterfront area with stunning views of Lake Champlain and the Adirondack Mountains. Enjoy a peaceful walk along the boardwalk, relax on the grassy lawn, and catch a beautiful lakeside sunset.

Accommodation Recommendation: The Hotel Vermont offers comfortable accommodations with a touch of rustic elegance and easy access to downtown Burlington.

Key Attractions: Church Street Marketplace, Burlington Bike Path, ArtsRiot Food Truck Stop, Shelburne Museum, Burlington breweries, Waterfront Park.

Pro Tip: Don’t miss the opportunity to try some delicious Vermont maple syrup. Many local shops in Burlington offer a variety of maple products, from syrup to candies and even maple-infused spirits.

Day 13: Stowe and Woodstock

On day 13 of your New England road trip, venture to two charming towns in Vermont – Stowe and Woodstock. These picturesque destinations offer a combination of natural beauty, quaint charm, and outdoor adventures.

Start your day in Stowe, a renowned destination for outdoor enthusiasts and nature lovers. Begin by exploring Stowe Mountain Resort, where you can take a scenic gondola ride to the summit and enjoy panoramic views of the Green Mountains. If you’re feeling adventurous, consider hiking one of the many trails in the area, such as the popular Stowe Pinnacle Trail.

Next, visit the Trapp Family Lodge, made famous by the von Trapp family of “The Sound of Music” fame. Take a walk around the beautiful property, enjoy the stunning mountain views, and indulge in a delicious Austrian-inspired meal at one of the onsite restaurants.

In the afternoon, make your way to Woodstock, a postcard-perfect village with picturesque streets and historic buildings. Take a leisurely walk around the village green, surrounded by classic New England-style houses and charming shops.

Visit the Billings Farm and Museum, a working dairy farm that offers insight into Vermont’s rural heritage. Learn about traditional farming practices, meet the farm animals, and explore the interactive exhibits that showcase the history of the region.

End your day with a visit to Quechee Gorge, often referred to as the “Grand Canyon of the East.” Marvel at the stunning views of the gorge and the Ottauquechee River as you stroll along the trails and bridges. Don’t forget to stop by the nearby Quechee Gorge Village for some shopping and a bite to eat.

Accommodation Recommendation: The Woodstock Inn & Resort, located in the heart of Woodstock, offers luxurious accommodations and a charming Vermont ambiance.

Key Attractions: Stowe Mountain Resort, Stowe Pinnacle Trail, Trapp Family Lodge, Woodstock village, Billings Farm and Museum, Quechee Gorge.

Pro Tip: Don’t miss the chance to taste some locally produced Vermont cheese. Visit a nearby cheese farm or stop by one of the specialty cheese shops in Stowe or Woodstock to sample and purchase some delicious artisanal cheeses.

Day 14: Berkshires, Massachusetts

On the final day of your New England road trip, explore the scenic beauty and cultural delights of the Berkshires in Massachusetts. Nestled in the rolling hills of western Massachusetts, the Berkshires offer a blend of natural beauty, artistic heritage, and charming towns.

Start your day by visiting the iconic Tanglewood, the summer home of the Boston Symphony Orchestra. Take a stroll through the beautiful grounds, enjoy a picnic on the lawn, and immerse yourself in the world of classical music at one of the outdoor concerts.

Next, make your way to the quaint town of Stockbridge. Visit the Norman Rockwell Museum to admire the works of the beloved American artist known for capturing the essence of everyday life. Explore the charming streets, browse through the boutique shops, and enjoy a delicious New England meal at one of the local eateries.

In the afternoon, journey to Mount Greylock, the highest peak in Massachusetts. Drive or hike to the summit to enjoy breathtaking views of the surrounding mountains and valleys. Explore the scenic trails that wind through the forested slopes, keeping an eye out for wildlife and enjoying the tranquility of nature.

Continue your Berkshires exploration by visiting the charming town of Lenox. Explore the historic downtown area, stroll along the tree-lined streets, and visit art galleries and unique shops. Lenox is also home to The Mount, the former estate of author Edith Wharton. Take a guided tour of the house and gardens to learn about Wharton’s life and literary career.

As the day winds down, head to the Jacob’s Pillow Dance Festival in Becket. This internationally renowned dance center hosts performances by world-class dance companies and offers workshops and events that celebrate the art of dance.

Accommodation Recommendation: The Porches Inn at MASS MoCA in North Adams provides unique and cozy accommodations with an artsy vibe, perfect for fully experiencing the Berkshires’ cultural scene.

Key Attractions: Tanglewood, Norman Rockwell Museum, Stockbridge, Mount Greylock, Lenox, The Mount, Jacob’s Pillow Dance Festival.

Pro Tip: During your visit, consider attending one of the many seasonal festivals and events that take place in the Berkshires, such as the Berkshire International Film Festival or the Berkshire Craft Fair. These events showcase the vibrant arts and culture scene in the region.

Conclusion

Congratulations! You have just completed an incredible 14-day New England road trip, exploring the diverse landscapes, rich history, and captivating culture of this region. From the bustling streets of Boston to the picturesque coastal towns, majestic mountains, and charming villages, you have experienced a true immersion into the beauty and charm of New England.

Throughout your journey, you have explored iconic landmarks and hidden gems, indulged in delicious seafood, immersed yourself in history at museums and historic sites, and enjoyed the natural wonders of national parks and scenic roadways. Each destination has offered a unique experience, allowing you to appreciate the rich heritage and natural beauty that New England has to offer.

Whether you are a history buff, nature lover, food enthusiast, or art aficionado, New England has something for everyone. The region’s vibrant cities, charming coastal towns, and picturesque landscapes provide a perfect backdrop for adventure, relaxation, and cultural exploration.

As you conclude your road trip, take a moment to reflect on the memories you’ve made, the breathtaking sights you’ve seen, and the experiences you’ve had. New England’s rich history, stunning landscapes, and warm hospitality have surely left a lasting impression.

Remember, this road trip itinerary is just a starting point. New England is a vast region with countless attractions and hidden treasures. Feel free to extend your trip, explore different routes, or revisit your favorite destinations in the future.

Thank you for joining us on this journey through New England. We hope you have enjoyed the enchanting landscapes, fascinating history, and warm hospitality that this region has to offer. Safe travels and may your future adventures be filled with joy, discovery, and cherished memories!