40 days in Massachusetts Itinerary

40 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner

Make it your trip
Fly to Bradley International Airport, Drive to Lenox
1
Lenox
— 4 nights
Drive
2
Pittsfield
— 4 nights
Drive
3
Springfield
— 4 nights
Drive
4
Salem
— 3 nights
Drive
5
Boston
— 4 nights
Drive
6
Plymouth
— 4 nights
Drive
7
Dennis
— 4 nights
Drive
8
Provincetown
— 3 nights
Taxi to Hyannis, MA, Ferry to Nantucket
9
Nantucket
— 8 nights
Fly

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Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. The Mount, Edith Wharton's Home and Old Rhinebeck Aerodrome will appeal to museum buffs. Satisfy your inner culture vulture at Vanderbilt Mansion National Historic Site and National Shrine of the Divine Mercy. And it doesn't end there: take in the awesome beauty at Monument Mountain, look for all kinds of wild species at Pleasant Valley Sanctuary, steep yourself in history at Chesterwood Museum, and admire the landmark architecture of Ventfort Hall Mansion and Gilded Age Museum.

For where to stay, more things to do, reviews, and more tourist information, refer to the Lenox road trip tool.

Stockholm, Sweden to Lenox is an approximately 22.5-hour combination of flight and car. The time zone difference when traveling from Stockholm to Lenox is minus 6 hours. While traveling from Stockholm, expect somewhat warmer days and about the same nights in Lenox, ranging from highs of 27°C to lows of 13°C. Finish your sightseeing early on the 6th (Sat) so you can drive to Pittsfield.

Things to do in Lenox

Historic Sites · Museums · Parks · Wildlife

Side Trips

Pittsfield

— 4 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Let the collections at MASS MoCA and Bennington Museum capture your imagination. Your inner history buff will appreciate Hancock Shaker Village and Herman Melville's Arrowhead. Venture out of the city with trips to North Adams Museum of History & Science (in North Adams), Lye Brook Falls (in Manchester) and Williams College Museum of Art (in Williamstown). And it doesn't end there: see the interesting displays at Berkshire Museum, get your game on at The Berkshire Carousel, hit the slopes at Jiminy Peak Mountain Resort, and trek along Ashuwillticook Rail Trail.

For photos, reviews, and other tourist information, read our Pittsfield attractions planner.

Pittsfield is very close to Lenox. Expect a daytime high around 27°C in June, and nighttime lows around 13°C. Cap off your sightseeing on the 10th (Wed) early enough to go by car to Springfield.

Things to do in Pittsfield

Museums · Parks · Historic Sites · Outdoors

Side Trips

Springfield

— 4 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Visit Springfield Armory National Historic Site and Harriet Beecher Stowe Center for their historical value. Step off the beaten path and head to Wadsworth Atheneum Museum of Art and Dinosaur State Park. Venture out of the city with trips to Emily Dickinson Museum (in Amherst), Hill-Stead Museum (in Farmington) and New Britain Museum of American Art (in New Britain). Next up on the itinerary: see the interesting displays at Connecticut River Museum, get great views at Castle Craig, and appreciate the history behind Dr. Seuss National Memorial Sculpture Garden.

For traveler tips, ratings, photos, and tourist information, use the Springfield day trip planner.

You can drive from Pittsfield to Springfield in 1.5 hours. In June, daytime highs in Springfield are 30°C, while nighttime lows are 14°C. Wrap up your sightseeing on the 14th (Sun) early enough to drive to Salem.

Things to do in Springfield

Museums · Historic Sites · Parks

Side Trips

Salem

— 3 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Your cultural itinerary includes sights like Count Orlok's Nightmare Gallery and Cape Ann Museum. Step out of the city life by going to Good Harbor Beach and Crane Beach. And it doesn't end there: enjoy the sea views from Chandler Hovey Park, contemplate the long history of Salem Maritime National Historic Site, examine the collection at Salem Witch Museum, and look for gifts at Hex: Old World Witchery.

To see photos, traveler tips, more things to do, and more tourist information, use the Salem road trip site.

Drive from Springfield to Salem in 2 hours. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 28°C, and evening lows to 15°C. Cap off your sightseeing on the 17th (Wed) early enough to go by car to Boston.

Things to do in Salem

Museums · Beaches · Parks · Outdoors

Side Trips

Boston

— 4 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
You'll explore the less-touristy side of things at Old State House and HarborWalk. Popular historic sites such as Freedom Trail and Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill are in your itinerary. There's much more to do: get engrossed in the history at John F. Kennedy Presidential Museum & Library, steep yourself in history at Charlestown Navy Yard, explore the galleries of The Paul Revere House, and take in the spiritual surroundings of Trinity Church.

To find where to stay, reviews, and other tourist information, read our Boston visit planner.

Drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. In June in Boston, expect temperatures between 28°C during the day and 18°C at night. Finish your sightseeing early on the 21st (Sun) so you can drive to Plymouth.

Things to do in Boston

Historic Sites · Museums · Neighborhoods · Shopping

Plymouth

— 4 nights

America's Hometown

Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Deepen your sense of the past at sights like National Monument to the Forefathers and Mayflower II. New Bedford Whaling Museum and The Jenney are good opportunities to explore the local culture. Change things up with these side-trips from Plymouth: Cape Cod Canal (in Buzzards Bay) and Falmouth (Highfield Hall & Gardens & Shining Sea Bikeway). There's lots more to do: stroll the grounds of Burial Hill, see the interesting displays at Heritage Museums & Gardens, contemplate the long history of Hedge House, and take an in-depth tour of Pilgrim Hall Museum.

For other places to visit, photos, ratings, and more tourist information, you can read our Plymouth road trip website.

You can drive from Boston to Plymouth in an hour. Alternatively, you can take a train; or take a bus. In June, plan for daily highs up to 28°C, and evening lows to 15°C. Wrap up your sightseeing on the 25th (Thu) to allow time to drive to Dennis.

Things to do in Plymouth

Museums · Historic Sites · Parks · Trails

Side Trips

Dennis

— 4 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Visiting Mayflower Beach and Harding Beach will get you outdoors. Get some historical perspective at Chatham Marconi Maritime Center and Fort Hill Rural Historic District. Change things up with these side-trips from Dennis: Coast Guard Beach (in Eastham) and Chatham Lighthouse Beach (in Chatham). There's much more to do: see the interesting displays at Whydah Pirate Museum, tour the pleasant surroundings at Corporation Beach, enjoy the sand and surf at First Encounter Beach, and pick up a one of a kind souvenir at Maps of Antiquity.

To see traveler tips, other places to visit, more things to do, and other tourist information, you can read our Dennis trip itinerary website.

Traveling by car from Plymouth to Dennis takes an hour. Expect a daytime high around 26°C in June, and nighttime lows around 17°C. Finish up your sightseeing early on the 29th (Mon) so you can go by car to Provincetown.

Things to do in Dennis

Beaches · Parks · Outdoors · Historic Sites

Side Trips

Provincetown

— 3 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Wellfleet Bay Wildlife Sanctuary and Sea Space Marine Discovery Center are good opportunities to explore the local culture. We've included these beaches for you: Herring Cove Beach and Marconi Beach. There's much more to do: kick back and relax at Long Point, look for all kinds of wild species at Beech Forest, Provincetown, cast your line with a fishing tour, and grab your bike and head to Province Lands Bike Trail.

To see maps, ratings, photos, and more tourist information, refer to the Provincetown attractions planning site.

Traveling by car from Dennis to Provincetown takes an hour. In June, daily temperatures in Provincetown can reach 26°C, while at night they dip to 15°C. Finish your sightseeing early on the 2nd (Thu) so you can travel to Nantucket.

Things to do in Provincetown

Parks · Outdoors · Wildlife · Beaches

Side Trip

Nantucket

— 8 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Take a break from the city and head to Madaket Beach and Siasconset Beach. Satisfy your inner culture vulture at Cisco Brewers and Great Point Light. There's much more to do: enjoy the sea views from Sankaty Head Lighthouse, kick back and relax at Children's Beach, steep yourself in history at Wauwinet, and take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To see photos, traveler tips, ratings, and other tourist information, read Nantucket sightseeing planner.

Traveling by combination of taxi and ferry from Provincetown to Nantucket takes 3 hours. Alternatively, you can do a combination of bus and ferry. In July in Nantucket, expect temperatures between 28°C during the day and 20°C at night. Wrap up your sightseeing on the 10th (Fri) to allow time to travel back home.

Things to do in Nantucket

Outdoors · Beaches · Parks · Historic Sites

Massachusetts travel guide

4.3
History Museums · Art Museums · Historic Walking Areas
The Bay State
Known as the "Bay State" because of the three bays dominating its coastline, Massachusetts has played a significant cultural and commercial role through most of the country's history. An increasingly popular vacation destination for foreign travelers, Massachusetts offers numerous places to visit, ranging from historical sites to modern urban centers famous for their culinary, art, and nightlife scenes. With the majority of its population living in and around the city of Boston, in the 20th century Massachusetts went from a state largely dependent on fishing and agriculture to the country's leader in higher education, healthcare, high technology, and financial services. Home to renowned universities and research centers, the state's cities attract a young crowd of students, scientists, artists, and business professionals.