New England Road Trip Itinerary
The New England Road Trip is a great way to explore the beauty of the northeastern United States. Starting in Boston, Massachusetts and ending in the same city, the trip covers 3111 km and takes about 20 days to complete. The best time to drive this route is in the spring or fall season when the weather is mild and the colors of the landscape are at their best.
The route winds through some of the most picturesque towns in the region, including Rockport, Ellsworth, Eastport, Milo, Lancaster, Alburgh, Manchester, Stamford, New Haven, and Newport. Along the way, travelers can explore historical sites, take in the stunning landscapes, and enjoy excellent road conditions.
This road trip is an unforgettable experience and is suitable for all drivers. It is recommended to plan for a high budget to get the most out of this journey, but the memories and sights you will experience make it well worth the effort.
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3,111 km
route length
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START
Boston
Distance 3,111 km
Driving time 43.3 h
Pace: fast
933.2 kWh
Airports
BOS
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Boston is the perfect starting point for an amazing road trip through New England. Located on the east coast of the United States, it’s easy to get to with Logan International Airport (IATA: BOS) as the main gateway to the city. Car rental is available at the airport for those who wish to start their adventure straight away.
The city of Boston has much to offer, from its diverse culture and history to its vibrant nightlife. Make sure to visit the Freedom Trail, a 2.5-mile walking path that takes you through 16 historically significant locations. Follow the trail to admire the architecture of the Old North Church, the oldest standing church in the city, and the USS Constitution, the world’s oldest commissioned warship.
For a taste of the city’s culture, take a stroll through Harvard Square and explore the many shops and restaurants. Or take a walk along the Charles River Esplanade to admire the stunning views of the city skyline.
No trip to Boston would be complete without paying a visit to Fenway Park, the oldest Major League Baseball stadium in the US. With its passionate fans and unique atmosphere, Fenway Park is a must-see for any baseball enthusiast.
Whether you’re here to explore the city’s rich history, enjoy its vibrant culture, or simply soak in the atmosphere of Fenway Park, Boston is the perfect place to begin your “New England Road Trip”.
1
Boston
- Rockport
Distance 58 km
Driving time 1.5 h
Pace: modest
15.2 kWh
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Ready to explore the beauty of New England? Then take your car and hit the road from Boston to Cape Ann and Rockport! This 36-mile route will take you less than two hours, so you can make a day trip out of it.
Start your journey in the historical city of Boston, then head out to the seaside town of Gloucester and explore its beautiful harbor. Don't forget to visit the lighthouse and the Fisherman's Memorial. After that, take a short drive to the charming town of Rockport, where you can explore the breathtaking coastline. Don't miss the famous Motif No. 1, the most painted fishing shack in America.
On your way back, make sure to visit the picturesque seaside village of Cape Ann. Here, you can explore the oldest fishing village in the country and take a stroll along the rocky coastline.
Don't forget to check the "Itinerary" of this stage for more information about attractions, accommodation options, recommended restaurants, and campsites along the route. Have a safe and enjoyable journey!
Rockport - United States - North America - Road Trip - Wikimedia Commons
Rockport - United States - North America - Road Trip - Wikimedia Commons
Rockport - United States - North America - Road Trip - www.wallpaperflare.com
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2
Rockport
- Portsmouth
Distance 84 km
Driving time 1.5 h
Pace: modest
21.9 kWh
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Embark on an unforgettable journey that starts in Rockport, United States and ends in Portsmouth, United States. This 52-mile (83.7 km) stage of your road-trip will take you less than 2 hours.
As you drive, make sure to take in the stunning scenery and take note of the historical sites.
First, you will be passing through Cape Ann, a beautiful region with a rich history. There, you can visit sites like the Halibut Point State Park, and the Cape Ann Museum.
Once you reach Portsmouth, you can explore the Strawbery Banke Museum, the John Paul Jones House, and the USS Albacore Museum.
All these places will give you a unique insight into the history and culture of the region.
For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage.
This is one of the stages of a larger tour, so make sure to enjoy every moment of it.
Portsmouth - United States - North America - Road Trip - Wikimedia Commons
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3
Portsmouth
- Ellsworth
Distance 307 km
Driving time 3.7 h
Pace: fast
92.0 kWh
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Are you ready for a great road trip from Portsmouth to Ellsworth? This 191mi journey will take you less than 4 hours and you will have the chance to visit some of the most interesting places in both cities.
Starting from Portsmouth, you can explore the Prescott Park, a 10-acre riverside park, or the Strawbery Banke Museum, a living history museum with interactive exhibits. You can also take a walk through the South Mill Pond, a beautiful natural area located in the heart of the city.
Continuing your journey, you will reach Ellsworth, where you can visit the Woodlawn Museum, a National Historic Landmark, or the Ellsworth Historical Society. You can also take a stroll around the Union River, a beautiful natural area full of wildlife.
These are just some of the places you can visit during your road trip from Portsmouth to Ellsworth. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage. Enjoy your trip!
Ellsworth - United States - North America - Road Trip - Wikimedia Commons
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4
Ellsworth
- Milbridge
Distance 134 km
Driving time 2.1 h
Pace: fast
40.2 kWh
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Start your road trip in Ellsworth, a vibrant town in the United States, and take a journey of 83 miles to discover the most interesting places in Acadia National Park and Milbridge. Along the way, you will be amazed by the picturesque landscapes and attractions. Along the route, you can find the Echo Lake Beach, a perfect spot for swimming and relaxing. You can also take a stroll around the Jordan Pond House and admire its stunning views. Moreover, you can explore the many trails and paths of the Acadia National Park, such as the Beehive Trail, the Precipice Trail, and the Cadillac Mountain Trail. Afterward, you can visit Milbridge and its historical sites, such as the Milbridge Historical Society Museum. The journey will take you fewer than 3 hours, so you can enjoy a pleasant road trip. Make sure to check the "Itinerary" of this stage for more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route.
Milbridge - United States - North America - Road Trip - Wikimedia Commons
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5
Milbridge
- Eastport
Distance 116 km
Driving time 1.5 h
Pace: fast
34.9 kWh
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Embark on a 72mi journey through Maine's Big Sur and explore the wonders of Milbridge, Eastport and all the places in between. In less than 2 hours, you will be able to experience the historical sites, beautiful landscapes and charming towns that make this region so special. Take a moment to appreciate the rolling hills, the blueberry fields and the rocky coastline. As you travel, you'll find plenty of opportunities to stop and explore the local attractions. Visit the lighthouses, explore the old forts, and take a stroll along the beach. Be sure to take your time and enjoy the scenic views. There's so much to see and do on this road trip, so be sure to take plenty of photos and make some lasting memories. Don't forget to check out the Itinerary for more information on attractions, accommodation options, recommended restaurants, and campsites along the route. So, what are you waiting for? Let's hit the road and explore Maine's Big Sur!
Eastport - United States - North America - Road Trip - Wikimedia Commons
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6
Eastport
- Houlton
Distance 190 km
Driving time 2.6 h
Pace: fast
57.1 kWh
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Welcome to the Eastport - Houlton road trip! This 118mi journey will take you fewer than 3 hours and will take you through some of the most interesting places in the area.
Starting in Eastport, you will be able to explore the beautiful Moosehorn National Wildlife Refuge, which offers plenty of outdoor activities, like hiking, bird watching, and kayaking.
Further down the road, you will come across the beautiful town of Calais. Here you can visit the St. Croix Island International Historic Site, which will give you a glimpse into the past.
The next stop is in Machias, where you can explore the Machias River Wildlife Management Area and the Machias River State Park. Here you can enjoy a variety of outdoor activities, including fishing, canoeing, and swimming.
Finally, you will arrive in Houlton, a small town with plenty of history and charm. Here you can visit the Aroostook State Park, which offers plenty of recreational activities and stunning views.
For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the "Itinerary" of this stage. Enjoy your road trip!
Houlton - United States - North America - Road Trip - Wikimedia Commons
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7
Houlton
- Milo
Distance 174 km
Driving time 2.1 h
Pace: fast
52.3 kWh
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Welcome to the Houlton-Milo road trip stage! This journey of 108 miles will take you less than 3 hours and will definitely be a memorable experience.
Starting in Houlton, you can visit the Aroostook State Park, a great spot for outdoor activities, or the Houlton Historical Museum, a great place to learn about the local history.
As you drive towards Milo, you will pass through the small towns of Littleton and Brownville. Make sure to take a break and visit the local shops and cafes.
Finally, you will arrive in Milo, home of the Sebec Lake and the Piscataquis River. Here you can enjoy a relaxing day on the lake, or explore the area's many hiking trails.
This stage is just a part of a larger tour, and more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route is available in the "Itinerary" of this stage.
Enjoy your Houlton-Milo road trip!
Milo - United States - North America - Road Trip - Wikimedia Commons
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8
Milo
- Eustis
Distance 169 km
Driving time 2.4 h
Pace: fast
50.6 kWh
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Welcome, road-trippers! This stage of your tour will start in Milo, United States, and end in Eustis, a journey of 105mi that will take you fewer than 3 hours.
The first stop in Milo is the Piscataquis River, a great spot to take a break and enjoy the views of the river and the nearby hills. The second stop is the Sebec Lake, a great place for a picnic or a swim. The last stop in Milo is the Sebec Lake Public Beach, a great spot to relax and enjoy the sun.
When you reach Eustis, make sure to visit the Flagstaff Lake, a great spot to take a break and enjoy the views of the lake and the nearby mountains. The second stop in Eustis is the Eustis Historical Society, a great place to learn about the history of the town and the surrounding area. The last stop in Eustis is the Eustis Village Green, a great spot to relax and take in the beauty of the town.
For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the "Itinerary" of this stage. Enjoy your road trip!
Eustis - United States - North America - Road Trip - Wikimedia Commons
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9
Eustis
- Lancaster
Distance 238 km
Driving time 3.4 h
Pace: fast
71.5 kWh
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Welcome road-trippers! Let's explore the 148-mile journey from Eustis to Lancaster. It will take you fewer than 4 hours to get there, so it's the perfect distance for a day trip.
Start your journey in Eustis. This small town is home to the Eustis Historical Museum and Preservation Society, where you can learn about the history of the area. Then, head to the nearby Lake Eustis, where you can take a boat ride and enjoy the stunning views.
Next, take a drive to the city of Tavares. Here, you can visit the Wooton Park, a large park with a playground, a pavilion, and a beautiful lake. Then, head to the Tavares Seaplane Base, where you can get a closer look at the seaplanes.
Continue your road trip to Leesburg, where you can explore the Venetian Gardens, a beautiful park with a lake and a walking trail. Then, head to the Lake Square Mall, where you can find a variety of shops and restaurants.
Finally, your journey will end in Lancaster. Here, you can explore the Lancaster Historical Museum, where you can learn about the history of the area. Then, you can visit the nearby Lancaster Park, a large park with a playground, a walking trail, and a lake.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage. Enjoy your journey!
Lancaster - United States - North America - Road Trip - www.wallpaperflare.com
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10
Lancaster
- Alburgh
Distance 329 km
Driving time 4.2 h
Pace: fast
98.6 kWh
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Are you ready for an amazing road trip from Lancaster to Alburgh through the White Mountains? This 204mi journey will take you less than 5 hours, so you will have plenty of time to explore the most interesting places along the way.
Start your journey with a visit to the White Mountains, where you will be able to admire the picturesque landscapes and take a hike in the area. Don't forget to take your camera with you to capture the breathtaking views!
Continue your journey to Alburgh, where you can explore the local attractions and enjoy the unique atmosphere of the city. You can also take a stroll along the beach or visit some of the local restaurants.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the Itinerary of this stage. Get ready for an unforgettable road trip!
Alburgh - United States - North America - Road Trip - en.wikipedia.org
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11
Alburgh
- Manchester
Distance 243 km
Driving time 3.4 h
Pace: fast
73.0 kWh
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Are you looking for a scenic road trip to explore the beauty of Lake Champlain? Start your journey in Alburgh, United States and drive through the magnificent Lake Champlain. Along the way, you will be able to enjoy the stunning views of the lake, its islands, and the Adirondack Mountains. The entire journey will take you fewer than 4 hours and will cover a distance of 151mi.
The first stop on your journey should be the Alburgh Dunes State Park, where you can observe the magnificent wildlife of the region. You can also take a boat ride to the nearby islands and explore the various historical sites. Further down the road, you can take a break at the Ausable Chasm and enjoy the breathtaking views of the river.
Continue your journey and you will reach the Burlington Waterfront, where you can explore the historical sites and enjoy the beauty of the lake. After that, you can drive to the Shelburne Museum and visit the various galleries and exhibits.
Your final destination is Manchester, where you can explore the various attractions and enjoy the peaceful atmosphere of the city. Make sure to take some time to visit the Bennington Battle Monument, a National Historic Landmark.
Don't forget to check the "Itinerary" of this stage for more information about attractions, accommodation options, recommended restaurants, and campsites along the route. Enjoy your journey!
Manchester - United States - North America - Road Trip - commons.wikimedia.org
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12
Manchester
- Stamford
Distance 389 km
Driving time 4.8 h
Pace: fast
116.6 kWh
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Start your road trip in Manchester, United States and explore the Merritt Parkway! This 242mi journey will take you less than 5 hours to complete and you'll get to see some of the most interesting places along the way. Your first stop should be the Housatonic Museum of Art in Bridgeport, Connecticut. Here you can explore the works of local and international artists and learn about the history of the area. Next, you'll make your way to the Stamford Museum and Nature Center, where you can observe wildlife, explore the gardens, and take part in educational programs. After that, you'll make your way to the Stamford Town Center, a shopping and dining destination with plenty of options. Finally, you'll end your journey in Stamford, Connecticut. Don't forget to check out the Stamford Historical Society, which offers a variety of exhibits and educational programs. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the "Itinerary" of this stage. Enjoy your road trip!
Stamford - United States - North America - Road Trip - Wikimedia Commons
Stamford - United States - North America - Road Trip - Wikimedia Commons
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13
Stamford
- New Haven
Distance 69 km
Driving time 1.3 h
Pace: modest
18.0 kWh
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Welcome, road-trippers! Let's explore the 43mi journey from Stamford to New Haven, a drive that will take you less than 2 hours.
Your first stop should be the Stamford Museum & Nature Center. This museum is a great place to learn about the city's history and explore the natural beauty of the area. You can also find a variety of exhibits and activities for the whole family.
Next, you should make your way to the Maritime Aquarium at Norwalk. Here, you can explore the wonders of the sea, including sharks, seals, sea turtles, and more. Plus, you can get up close and personal with the creatures in their touch tank.
Finally, you should end your journey in New Haven. Here, you can visit the Yale University Art Gallery, which houses a collection of art from around the world. You can also explore the Yale Peabody Museum of Natural History, which showcases an impressive collection of fossils, minerals, and more.
That's it for this stage of your road trip! For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, check out the "Itinerary" of this stage. Have a great journey!
New Haven - United States - North America - Road Trip - www.goodfreephotos.com
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14
New Haven
- Newport
Distance 168 km
Driving time 2.0 h
Pace: fast
50.5 kWh
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Welcome to the road trip stage that starts in New Haven, United States, and ends in Newport! This 105-mile journey will take you no more than two hours to complete. Along the way, you’ll have the chance to explore some of the most interesting places in the region.
In New Haven, you can visit the Yale University campus, the historic Shubert Theatre, and the New Haven Green, a 16-acre public park in the heart of the city. If you’re looking for a bite to eat, try the iconic Frank Pepe Pizzeria.
As you drive to Newport, you’ll pass through some picturesque towns and villages. Once you arrive in Newport, take some time to explore the city’s beautiful coastline. You can visit the famous Newport Mansions, the International Tennis Hall of Fame, and the Touro Synagogue National Historic Site.
No matter what you choose to do, you’re sure to have an unforgettable experience. Be sure to check the “Itinerary” of this stage for more information on attractions, accommodation options, recommended restaurants, and campsites along the route. Enjoy your trip!
Newport - United States - North America - Road Trip - Wikimedia Commons
Newport - United States - North America - Road Trip - Wikimedia Commons
Newport - United States - North America - Road Trip - pxhere.com
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15
Newport
- Provincetown
Distance 234 km
Driving time 3.7 h
Pace: fast
70.2 kWh
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Embark on a 145 mi journey to explore the most interesting places of Newport, Cape Cod and Provincetown. Start your trip from Newport, a coastal city in Rhode Island, and enjoy its beautiful scenery, its historical sites, and its vibrant culture. Then, head to Cape Cod, a peninsula located in the southeastern corner of Massachusetts. Here, you will find a variety of attractions, from its beautiful beaches to its quaint villages. Finally, arrive in Provincetown, the most visited port in the area. Here, you can explore its unique landscape and its many historical sites. All of this can be done in less than 4 hours of driving.
While on the road, don't forget to pay attention to the historical sites, as they will give you a better understanding of the region's past. For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, make sure to check the "Itinerary" of this stage.
This is one of the stages of a larger tour, and you will surely find it to be an unforgettable experience. So, start your engine and get ready to explore Newport, Cape Cod, and Provincetown!
Provincetown - United States - North America - Road Trip - Wikimedia Commons
Provincetown - United States - North America - Road Trip - Wikimedia Commons
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16
Provincetown
- Plymouth
Distance 131 km
Driving time 1.7 h
Pace: fast
39.3 kWh
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Embark on an exciting road trip from Provincetown to Plymouth and discover the beauty of Cape Cod. The 82-mile journey takes less than two hours to complete and is filled with historical sites and amazing views. Start your journey in Provincetown, where you can explore the Pilgrim Monument and the Provincetown Museum. As you drive along the coast, you will be able to take in the stunning views of the Atlantic Ocean. Make sure to stop in Hyannis and check out the John F. Kennedy Hyannis Museum and Main Street. Further down the road, you can visit the Plimoth Plantation and the Mayflower II in Plymouth. Along the way, you can find plenty of accommodations, restaurants, and campsites. Get ready for an unforgettable experience and don’t forget to check out the Itinerary for more information about attractions, accommodation options, recommended restaurants, and campsites.
Plymouth - United States - North America - Road Trip - www.flickr.com
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17
Plymouth
- Boston
Distance 76 km
Driving time 1.5 h
Pace: modest
19.8 kWh
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Welcome to the Plymouth to Boston road trip! This beautiful journey is only 47 miles long and can be completed in less than two hours. You’ll get to experience the historical sites of Plymouth and Boston, two cities with rich American history.
Starting in Plymouth, you can explore Plymouth Rock, the iconic symbol of the Mayflower Pilgrims’ arrival in 1620. You can also visit the Pilgrim Hall Museum, which features artifacts from the Pilgrims’ journey.
Heading to Boston, you’ll come across the Bunker Hill Monument, which commemorates the Battle of Bunker Hill in the American Revolutionary War. You can also explore the USS Constitution Museum, which showcases the history of the USS Constitution, the oldest commissioned warship afloat in the world.
Be sure to take your time to explore these two amazing cities and all their attractions. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, check out the Itinerary of this stage. Enjoy your road trip!
Boston - United States - North America - Road Trip - Wikimedia Commons
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Boston
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The end of the road is near! The journey that started in the north of the United States is coming to an end in the vibrant city of Boston. Located in the Commonwealth of Massachusetts, this city offers endless possibilities to the explorer.
For starters, the iconic Freedom Trail takes visitors to 16 of the most important historical sites in the city, such as the Old North Church, Bunker Hill Monument, and the USS Constitution Museum. There are also plenty of museums to visit, such as the Museum of Fine Arts, which showcases artwork from around the world.
If you're a sports fan, you'll be delighted to know that Boston is a great place to watch a game. Home to the Red Sox, Celtics, Bruins and Patriots, there's no shortage of sports teams to cheer on.
For those looking for something a little more outdoorsy, Boston Common, the oldest public park in the United States, is a great place to explore. The area also has its fair share of parks, beaches, and walking trails.
If you're traveling by car, the closest international airport is Logan International Airport (BOS). From there, you can easily get to the city.
At the end of the New England Road Trip, Boston will be sure to leave you with unforgettable memories. So don't forget to explore this city and its surrounding areas before heading home.
New England Road Trip at a glance
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Start:
Boston
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End:
Boston
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Distance:
3,111 km
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Stay:
20 days
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Getting there:
Logan International Airport (BOS)
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When to drive:
May, June, July, August, September, October
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More info:
More info you can find in the "Itinerary" section at each stage.
Before you set off
The New England Road Trip is a captivating adventure through the northeastern United States, starting and ending in the vibrant city of Boston, Massachusetts. Covering an impressive distance of over 3111 km (1933 miles) and often taking around 20 days to complete, this journey invites travelers to explore the region's stunning beauty, rich history, and charming towns.
Key Destinations and Top Sights:
- Boston: The historic starting point, where you can walk the Freedom Trail, visit Faneuil Hall, and explore museums like the Museum of Fine Arts.
- Rockport: A picturesque coastal town celebrated for its art galleries, rocky beaches, and the iconic red fishing shack known as `Motif Number One.`
- Ellsworth: The gateway to Acadia National Park, where visitors can enjoy breathtaking landscapes, hiking trails, and the dramatic Cadillac Mountain.
- Eastport: The easternmost city in the contiguous U.S., offering charming shops, fresh seafood, and waterfront views, as well as the annual Pirate Festival.
- Milo ; Lancaster: Quaint towns that provide a window into traditional New England life, with opportunities to experience local agriculture and crafts.
- Alburgh: Nestled on a peninsula within Lake Champlain, this area is renowned for its serene natural scenery and opportunities for fishing and boating.
- Manchester: Home to upscale shopping and the grand Hildene, The Lincoln Family Home, which is the former estate of President Lincoln’s son, Robert Todd Lincoln.
- Stamford: A city that combines urban amenities with a New England small-town atmosphere, including parks and historical sites.
- New Haven: Famous for Yale University's beautiful campus, prestigious cultural institutions, and a thriving culinary scene.
- Newport: Renowned for its opulent Gilded Age mansions, such as The Breakers, and the scenic Cliff Walk, offering panoramic ocean views.
Best Time to Go:
Spring (May to June) and fall (September to October) are the most picturesque times to embark on this Road Trip, with pleasant weather and either the spring bloom or autumn foliage providing a stunning backdrop for your journey.
Potential Risks:
- Weather can be unpredictable, especially in transitional seasons, potentially impacting driving conditions.
- Popular tourist destinations may experience high traffic during peak seasons like summer and fall foliage weekends.
- Be cautious of wildlife crossings, particularly in rural and forested areas.
Interesting Facts for Roadtrippers:
- The Trip is accessible for drivers of all levels, with well-maintained Roads and clear signage.
- A higher budget will enhance the experience, allowing for indulgences in local cuisine, accommodations, and attractions.
- Advance planning is crucial, especially for accommodations and popular attractions, to ensure availability and the best experience.
A good choice for:
Embarking on the New England Road Trip is an opportunity to delve into a blend of America's past and present. From the cobblestone streets of Boston to the majestic shores of Acadia, the journey weaves through landscapes that inspired poets and played pivotal roles in U.S. history. Whether you're savoring fresh lobster by the ocean or marveling at autumn’s fiery hues, this Road Trip is an unforgettable way to discover the essence of New England.
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