Massachusetts Road Trip Itinerary
Explore the beauty of Massachusetts with a 14-day road trip from Boston to Boston. Along the way, discover a variety of attractions, from the rocky coastline of Rockport to the serene beaches of Provincetown. The route also takes you to Greenfield, Springfield, Falmouth, Chatham, and Orleans. This 1056 km drive can be completed year-round, but is best experienced in the spring and summer when the weather is mild and the scenery is lush. Enjoy excellent road conditions, but be aware that some roads are curvy. With its diverse landscapes, charming towns, and stunning beaches, this road trip provides an unforgettable experience. While it may require a high budget, it's suitable for all drivers.
14
number of days
1,056 km
route length
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budget
family
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traffic direction
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START
Boston
Distance 1,056 km
Driving time 16.8 h
Pace: modest
274.4 kWh
Airports
BOS
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Boston is the perfect starting point for the Massachusetts Road Trip. Located in the Northeastern United States, it is the largest city in the region and has a wealth of sights and attractions to explore. Start your trip by visiting the iconic Freedom Trail, a 2.5 mile long path through the city that passes 16 of Boston’s most significant historical sites, including the site of the Boston Massacre and the Old North Church. After exploring the Freedom Trail, make sure to check out the iconic Boston Common, the country's oldest public park, and the adjacent Boston Public Garden, which features the famous Swan Boats.
Continue your journey by exploring some of Boston’s world-renowned museums, such as the Museum of Fine Arts, the Institute of Contemporary Art, and the Isabella Stewart Gardner Museum. After sightseeing, enjoy some of the city's excellent cuisine and nightlife. For those flying into Boston, the closest international airport is Logan International Airport (BOS). Passengers arriving by air can take advantage of car rental services at the airport, allowing for easy access to all of Boston’s attractions. Whether you have a few days or a few weeks in Boston, the city has something for everyone. Begin your Massachusetts Road Trip in Boston and explore all this amazing city has to offer.
1
Boston
- Rockport
Distance 63 km
Driving time 1.6 h
Pace: slow
14.4 kWh
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Begin your journey in Boston and enjoy the beautiful drive up the coast of Massachusetts to Rockport. On the way, you'll pass through Manchester-by-the-Sea, a charming coastal town with plenty of history. The drive is only 39 miles and takes less than 2 hours, but don't rush -- there's plenty to see along the way! As you wind your way up the coast, take in the scenic views and make sure to visit some of the historical sites. Once you arrive in Manchester-by-the-Sea, be sure to explore the town's quaint shops and restaurants. From there, it's only a short drive to Rockport, where you can enjoy a stroll along the harbor and take in the stunning views. Along the way, you'll find plenty of accommodation options, restaurants, and campsites to make your journey even more enjoyable. For more information about attractions, accommodation, restaurants, and campsites along the route, be sure to check the "Itinerary" of this stage. So, what are you waiting for? Hop in the car and start your 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
- Lawrence
Distance 66 km
Driving time 1.4 h
Pace: modest
17.2 kWh
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Begin your journey in Rockport, United States, and take the scenic route through Ocean View and Essex before ending in Lawrence. The total driving time is less than two hours and the distance is 41 miles. Enjoy the winding roads and the beautiful scenery as you make your way to Lawrence.
In Rockport, take the time to explore the beaches and the historic harbor. In Ocean View, you can find a variety of outdoor activities, from fishing to kayaking. In Essex, you can visit the historic sites and quaint shops.
When you arrive in Lawrence, you can explore the many parks and trails. There are also plenty of restaurants, shops, and galleries to explore.
No matter where you go on this journey, you’ll find plenty of things to do and see. For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the Itinerary of this stage. Enjoy your road trip!
Lawrence - United States - North America - Road Trip - commons.wikimedia.org
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3
Lawrence
- Greenfield
Distance 144 km
Driving time 1.6 h
Pace: fast
43.2 kWh
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Welcome to the Lawrence to Greenfield road trip stage! This journey is part of a larger tour, and promises to be an exciting one. You will cover 89mi in fewer than 2 hours, and get to explore the best of both cities.
In Lawrence, you can visit the Lawrence Art Center, the Spencer Museum of Art, and the University of Kansas Natural History Museum. If you're looking for some outdoor fun, you can head to Clinton State Park or the Lawrence Indoor Aquatic Center.
When you arrive in Greenfield, there is plenty to explore. Check out the New Century Fieldhouse, the Kansas Aviation Museum, or the Kansas Firefighters Museum. For nature lovers, the Santa Fe Trail and the Greenfield Park are great places to go.
For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, check out the "Itinerary" of this stage. Enjoy your trip!
Greenfield - United States - North America - Road Trip - Wikimedia Commons
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4
Greenfield
- Williamstown
Distance 68 km
Driving time 1.1 h
Pace: fast
20.4 kWh
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Are you ready for a fun and exciting road trip from Greenfield to Williamstown? This 42mi drive will take you less than two hours, and you'll get to enjoy some of the most scenic views in the area. The road is quite winding in some sections, so buckle up and get ready for the ride!
First, you'll start in Greenfield, where you can visit the historic Greenfield Village, the Henry Ford Museum, and the Greenfield Village Theater. Then, you can make a stop at the charming town of Saline, where you can explore the Saline Riverwalk and take a stroll through the picturesque downtown area.
Once you reach Williamstown, you can explore the Williamstown Historical Museum, the Williamstown Lake Park, and the Williamstown Community Arts Center. There are also plenty of great restaurants, shops, and other attractions to explore.
This is just one of the many stops on your road trip, so make sure to take some time to explore the area. For more information about attractions, accommodations, recommended restaurants, and campsites along the route, be sure to check out the "Itinerary" of this stage. Enjoy your journey!
Williamstown - United States - North America - Road Trip - www.pxfuel.com
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5
Williamstown
- Springfield
Distance 117 km
Driving time 1.7 h
Pace: fast
35.0 kWh
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Are you ready for an amazing road trip experience? Starting in Williamstown, United States, you will be driving for 72 miles and in less than 2 hours you will be in Springfield.
In Williamstown, make sure to visit the Williamstown Historic District which is listed in the National Register of Historic Places. It includes the oldest house in Williamstown and a variety of architectural styles.
When you reach Springfield, you must visit the Springfield Armory National Historic Site. It is the oldest armory in the United States and is home to the nation’s first armory. It is also a great place to learn about the history of the United States military.
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!
Springfield - United States - North America - Road Trip - Wikimedia Commons
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6
Springfield
- Providence
Distance 139 km
Driving time 1.5 h
Pace: fast
41.8 kWh
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Are you ready to embark on a road trip from Springfield to Providence? This leg of your journey is only 87mi and you can drive it in fewer than 2 hours.
Start your trip in Springfield, a city full of history, culture and entertainment. Visit the Springfield Museums, featuring four museums in one building, or take a stroll in Forest Park, the largest park in the city.
Continue your journey to Providence, the capital of Rhode Island. Here you can explore the city's rich history, art and culture. Admire the architecture of the State House or visit the Roger Williams Park Zoo. For a taste of the local culture, stroll down the cobblestone streets of Federal Hill and enjoy the local cuisine.
For more information about attractions, accommodation, recommended restaurants and campsites along the route, please check the "Itinerary" of this stage. Have a safe and pleasant journey!
Providence - United States - North America - Road Trip - www.flickr.com
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7
Providence
- Falmouth
Distance 112 km
Driving time 1.3 h
Pace: fast
33.5 kWh
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Are you ready for an amazing road trip from Providence to Falmouth? This stage of your journey will take you along a scenic route of 69 miles and less than 2 hours of driving.
Start your journey in Providence and make your way to Wareham. Here you can visit the Wankinco River, a peaceful and picturesque spot, perfect for a picnic. Make sure to take some photos of the river and its wildlife!
Continue your journey to Falmouth, where you can explore the Falmouth Historical Society and learn more about the town's history. You can also visit the Woods Hole Science Aquarium and the Marine Biological Laboratory.
Along the way, make sure to take in the beautiful scenery and enjoy the peaceful drive.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, please check the "Itinerary" of this stage. Enjoy the journey!
Falmouth - United States - North America - Road Trip - www.ihacom.ca
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8
Falmouth
- Chatham
Distance 73 km
Driving time 1.8 h
Pace: modest
19.0 kWh
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Welcome road-trippers! Get ready to explore the beautiful 45mi route from Falmouth to Chatham. The drive should take you fewer than 2 hours and you should definitely keep an eye out for the scenic road. In some sections, the road is very winding, so be careful and enjoy the journey. Along the way, you'll find several interesting places to visit, such as the Woods Hole Historical Museum, the Knob Hill Historic District, and the Chatham Lighthouse. You can also find several restaurants, hotels, and campsites in both towns. So don't forget to check the itinerary for more information about attractions, accommodation options, recommended restaurants, and campsites along the route. Have a great trip!
Chatham - United States - North America - Road Trip - www.wallpaperflare.com
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9
Chatham
- Provincetown
Distance 59 km
Driving time 1.0 h
Pace: modest
15.2 kWh
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Start your journey in Chatham, the perfect place to kick off your road trip. As you drive 36 miles to Truro, you'll be surrounded by the breathtaking beauty of the Cape Cod National Seashore. Make sure to keep your eyes open for historical sites and scenic roads. Once you arrive in Truro, you can explore its quaint streets and charming shops. After Truro, you'll continue your journey to Provincetown. This is the perfect place to end your journey, as it offers so many attractions and activities. From whale watching to art galleries, you'll find something to do for everyone. Don't forget to check out the iconic Pilgrim Monument and the Provincetown Museum. As you drive, keep your eyes open for the many lighthouses that dot the coastline. With a driving time of fewer than one hour, this is the perfect road trip stage to explore the beauty of Cape Cod. For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, check out the Itinerary of this stage.
Provincetown - United States - North America - Road Trip - Wikimedia Commons
Provincetown - United States - North America - Road Trip - Wikimedia Commons
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10
Provincetown
- Orleans
Distance 48 km
Driving time 0.9 h
Pace: modest
12.4 kWh
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Embark on a 30mi road trip from Provincetown to Orleans, via Wellfleet, and explore the beauty of Cape Cod. The drive will take you less than an hour, and you will be mesmerized by the picturesque views of the ocean, salt marshes, and lush green meadows along the way.
Start your journey in Provincetown, a quaint seaside village that is steeped in history. Visit the iconic Pilgrim Monument, the oldest all-granite structure in the United States, or explore the charming shops and restaurants on Commercial Street.
Continue your journey to Wellfleet, a charming fishing village with a rich maritime heritage. See the beautiful Wellfleet Harbor, visit the Wellfleet Historical Society, or check out the local seafood market.
Finally, end your road trip in Orleans, one of the oldest villages on Cape Cod. Take a stroll along the Nauset Marsh boardwalk, explore the local shops and galleries, or visit the Skaket Beach State Reservation.
For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, check out the "Itinerary" of this stage. Enjoy the journey!
Orleans - United States - North America - Road Trip - Wikimedia Commons
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11
Orleans
- Plymouth
Distance 92 km
Driving time 1.3 h
Pace: fast
27.6 kWh
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Start your journey in Orleans, a small town in the United States, and take the 57 miles drive to Barnstable. Along the way, you can take in the beautiful scenery and historical sites. Keep your eyes peeled for the old cranberry bogs and the iconic windmills that dot the landscape. If you're lucky, you might even spot some of the local wildlife. Once you reach Barnstable, you can visit the Cape Cod Museum of Natural History, or take a stroll along the beach. After exploring Barnstable, continue your journey to Plymouth, a historic town known as the birthplace of America. Here, you can explore the Mayflower II, Plymouth Rock, and the National Monument to the Forefathers. Additionally, there are plenty of shops, restaurants, and museums to explore. This road trip will take you fewer than two hours, and it's a great way to experience the beauty and history of the United States. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, be sure to check out the itinerary for this stage.
Plymouth - United States - North America - Road Trip - www.flickr.com
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12
Plymouth
- Boston
Distance 77 km
Driving time 1.5 h
Pace: modest
19.9 kWh
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Welcome to the Plymouth-Boston stage of your road trip! This stretch of the tour is about 48 miles long and can be completed in under two hours. You will be driving through some of the oldest towns in the United States, seeing historical sites that have been around for centuries. As you take in the scenery, make sure to keep an eye out for some of the most interesting places to visit.
In Plymouth, you can visit the Plymouth Rock, the site where the Pilgrims first landed in the New World. You can also check out Plimoth Plantation, a living history museum that recreates the Pilgrims' settlement of 1627.
In Boston, you can explore the Freedom Trail, a 2.5-mile long walking tour that takes you through some of the most important sites of the American Revolution. You can also visit the USS Constitution Museum, the oldest commissioned warship in the world.
For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, check out the Itinerary section of this stage. Enjoy your drive!
Boston - United States - North America - Road Trip - Wikimedia Commons
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Boston
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Boston, the capital of the Commonwealth of Massachusetts, is the perfect ending point for the "Massachusetts Road Trip". Located in the eastern United States, Boston is a beautiful city with plenty of history and interesting attractions.
Start your exploration of the city at the iconic Freedom Trail, a 2.5-mile-long path that passes by 16 historically significant sites. Learn about the American Revolution at the Paul Revere House and the USS Constitution Museum, and explore the unique architecture of the area.
If you’re looking for some outdoor fun, take a stroll through the Boston Common, which is the oldest public park in the country. The Public Garden, which is adjacent to the Common, is also worth a visit. Or, take a short drive to the nearby beaches of the South Shore.
No trip to Boston is complete without a visit to Fenway Park, home of the Red Sox. Whether you’re a fan or not, the park is a great place to take a tour, grab some food, and enjoy the atmosphere.
For those traveling by air, the closest international airport is Boston Logan International Airport (BOS). From there, it’s a short drive to the city, making it the perfect end to the "Massachusetts Road Trip".
Massachusetts Road Trip at a glance
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Start:
Boston
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End:
Boston
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Distance:
1,056 km
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Stay:
14 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
Embark on a captivating 14-day circular Road Trip that begins and ends in the historic city of Boston, Massachusetts. Covering a distance of approximately 1056 kilometers (656 miles), this journey will lead you through a tapestry of diverse landscapes, from the craggy shores of the Atlantic to serene sandy beaches, and through picturesque towns brimming with American history.
Key Destinations and Top Sights:
- Rockport: Immerse yourself in the stunning rocky coastlines and explore the vibrant art galleries and studios that make up this creative enclave.
- Provincetown: Experience the quiet beauty of Cape Cod's beaches and the bustling cultural scene of this historic LGBTQ+ friendly seaside town.
- Greenfield: Discover the idyllic rural landscapes and delve into the region's rich cultural heritage, including old mills and covered bridges.
- Springfield: Pay homage to the sport of basketball at the Naismith Memorial Basketball Hall of Fame and enjoy whimsical sculptures at the Dr. Seuss National Memorial Sculpture Garden.
- Falmouth: Stroll along serene beaches and take a short ferry ride to the enchanting Martha's Vineyard, known for its lighthouses, celebrity sightings, and classic New England charm.
- Chatham: Visit the iconic Chatham Lighthouse, snap pictures of the charming main street, and indulge in fresh seafood at local eateries.
- Orleans: Unwind on the expansive sands of Nauset Beach and sample mouthwatering seafood, reflecting the area's rich maritime traditions.
Best Time to Go:
The ideal time to take this Massachusetts Road Trip is during the spring and summer months when the weather is mild, and the landscape bursts with life. This period is perfect for enjoying outdoor activities and seeing the state's flora and fauna in full bloom.
Potential Risks:
Curvy coastal Roads require attentive driving, and it's wise to stay informed about weather forecasts to avoid the occasional Nor'easter or summer storm that can affect travel plans.
Interesting Facts for Roadtrippers:
- Massachusetts's landscape is incredibly varied, boasting a mix of bustling cityscapes like Boston and the tranquil retreats of Cape Cod.
- While Roads are generally well-maintained, planning for expenses is crucial, as accommodations and attractions can be pricey, especially during peak tourist seasons.
- The state is a treasure trove of American history, with opportunities to visit landmarks from the Revolutionary War, maritime museums, and the homes of literary giants like Herman Melville and Emily Dickinson.
A good choice for:
Traversing through Massachusetts on this Road Trip will provide an extraordinary exploration of the state's stunning natural vistas and historically rich towns. It's an ideal adventure for drivers who appreciate both the journey and the destination, offering a blend of recreation, education, and relaxation.
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