44 days in Massachusetts Itinerary

44 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary 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
— 5 nights
Drive
4
Salem
— 4 nights
Drive
5
Boston
— 5 nights
Drive
6
Plymouth
— 4 nights
Drive
7
Dennis
— 4 nights
Drive
8
Chatham
— 3 nights
Drive
9
Provincetown
— 4 nights
Taxi to Hyannis, MA, Ferry to Nantucket
10
Nantucket
— 5 nights
Fly

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Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Get a sense of the local culture at Vanderbilt Mansion National Historic Site and Frances Lehman Loeb Art Center at Vassar College. Get outdoors at Pleasant Valley Sanctuary and Concepts of Art Lenox Judaica. Explore Lenox's surroundings by going to Kaaterskill Falls (in Haines Falls), Eleanor Roosevelt National Historic Site (in Hyde Park) and Hudson River Maritime Museum (in Kingston). Next up on the itinerary: steep yourself in history at The Mount, Edith Wharton's Home, don't miss a visit to Lighthouse, and admire the landmark architecture of Ventfort Hall Mansion and Gilded Age Museum.

To see reviews, ratings, where to stay, and tourist information, refer to the Lenox road trip planning app.

Stockholm, Sweden to Lenox is an approximately 22.5-hour combination of flight and car. The time zone changes from Central European Standard Time (CET) to Eastern Standard Time (EST), which is usually a -6 hour difference. 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. Cap off your sightseeing on the 6th (Sat) early enough to go by car to Pittsfield.

Things to do in Lenox

Historic Sites · Museums · Parks · Nature

Side Trips

Pittsfield

— 4 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Get a sense of the local culture at MASS MoCA and Berkshire Museum. Popular historic sites such as Hancock Shaker Village and Robert Frost Stone House Museum are in your itinerary. Venture out of the city with trips to Manchester (Lye Brook Falls & Equinox Preservation Trust), Williams College Museum of Art (in Williamstown) and Mount Greylock State Reservation (in Lanesboro). There's lots more to do: admire the masterpieces at Bennington Museum, have some family-friendly fun at The Berkshire Carousel, and take in the spiritual surroundings of The Old First Church.

For traveler tips, maps, reviews, and more tourist information, read Pittsfield route builder app.

Pittsfield is just a stone's throw from Lenox. Expect a daytime high around 27°C in June, and nighttime lows around 13°C. Wrap up your sightseeing on the 10th (Wed) early enough to drive to Springfield.

Things to do in Pittsfield

Museums · Parks · Historic Sites · Nature

Side Trips

Springfield

— 5 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Springfield Museums and Wadsworth Atheneum Museum of Art are good opportunities to explore the local culture. Explore hidden gems such as Hammonasset Beach State Park and Historic Deerfield. Explore the numerous day-trip ideas around Springfield: Yale Peabody Museum of Natural History (in New Haven), Hill-Stead Museum (in Farmington) and Yankee Candle Flagship Store (in South Deerfield). Next up on the itinerary: see the interesting displays at New England Air Museum, appreciate the history behind Dr. Seuss National Memorial Sculpture Garden, learn about all things military at Springfield Armory National Historic Site, and try to win big at MGM Springfield.

To find maps, traveler tips, reviews, and more tourist information, read Springfield road trip planning tool.

You can drive from Pittsfield to Springfield in 1.5 hours. In June, plan for daily highs up to 30°C, and evening lows to 14°C. Finish your sightseeing early on the 15th (Mon) so you can drive to Salem.

Things to do in Springfield

Museums · Parks · Childrens Museums · Outdoors

Side Trips

Salem

— 4 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.
Escape the urban bustle at Halibut Point State Park and Good Harbor Beach. Step off the beaten path and head to Count Orlok's Nightmare Gallery and Cape Ann Museum. Change things up with these side-trips from Salem: Parker River National Wildlife Refuge (in Newburyport) and Crane Beach (in Ipswich). The adventure continues: stop by Crow Haven Corner, visit a coastal fixture at Derby Wharf Light Station, take an in-depth tour of The House of the Seven Gables, and browse the exhibits of Gedney House.

Use Inspirock's suggestions to plan your Salem trip and find the best activities and attractions for your vacation.

Getting from Springfield to Salem by car takes about 2 hours. Other options: take a bus; or take a train. In June in Salem, expect temperatures between 28°C during the day and 15°C at night. Finish your sightseeing early on the 19th (Fri) to allow enough time to drive to Boston.

Things to do in Salem

Parks · Museums · Historic Sites · Nature

Side Trips

Boston

— 5 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 discover tucked-away gems like Trinity Church and Rosecliff. Get outdoors at Adams National Historical Park and Wallis Sands State Beach. Venture out of the city with trips to Strawbery Banke Museum (in Portsmouth), Benefit Street (in Providence) and When Pigs Fly Company Store (in Kittery). Next up on the itinerary: ponder the world of politics at Massachusetts State House, get engrossed in the history at John F. Kennedy Presidential Museum & Library, take a stroll through Copley Square, and appreciate the history behind The Mapparium.

Make your Boston itinerary with Inspirock to find out what to see and where to go.

You can drive from Salem to Boston in an hour. Other options are to take a train; or take a bus. Expect a daytime high around 28°C in June, and nighttime lows around 18°C. Finish your sightseeing early on the 24th (Wed) so you can drive to Plymouth.

Things to do in Boston

Historic Sites · Museums · Parks · Neighborhoods

Side Trips

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.
Do some cultural sightseeing at Lizzie Borden House and The Jenney. National Monument to the Forefathers and Scituate Lighthouse will appeal to history buffs. Get out of town with these interesting Plymouth side-trips: Battleship Cove (in Fall River), Mashpee Commons (in Mashpee) and Shining Sea Bikeway (in Falmouth). There's still lots to do: take an in-depth tour of Pilgrim Hall Museum, examine the collection at Heritage Museums & Gardens, visit a coastal fixture at Nobska Point Lighthouse, and take in nature's colorful creations at Brewster Gardens.

To find traveler tips, reviews, photos, and tourist information, use the Plymouth travel route planning tool.

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. Finish up your sightseeing early on the 28th (Sun) so you can go by car to Dennis.

Things to do in Plymouth

Museums · Parks · Historic Sites · Outdoors

Side Trips

Dennis

— 4 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. You'll enjoy a bit of beach vacationing at Skaket Beach and Corporation Beach. Eschew the tourist crowds and head to First Encounter Beach and Nauset Lighthouse. Step out of Dennis to go to Eastham and see Coast Guard Beach, which is approximately 32 minutes away. The adventure continues: kick back and relax at Mayflower Beach, examine the collection at Edward Gorey House, pause for some serene contemplation at Church of the Transfiguration, and contemplate the long history of Doane Rock.

To see traveler tips, reviews, other places to visit, and other tourist information, go to the Dennis travel itinerary planner.

You can drive from Plymouth to Dennis in an hour. In June, plan for daily highs up to 26°C, and evening lows to 17°C. Wrap up your sightseeing on the 2nd (Thu) to allow time to drive to Chatham.

Things to do in Dennis

Beaches · Parks · Outdoors · Historic Sites

Side Trips

Chatham

— 3 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. You'll enjoy a bit of beach vacationing at Nauset Beach and Harding Beach. Take a break from the city and head to Monomoy National Wildlife Refuge and Red River Beach. There's much more to do: admire the masterpieces at Atwood Museum, stop by Maps of Antiquity, enjoy the sand and surf at Chatham Lighthouse Beach, and engage your brain at Chatham Marconi Maritime Center.

To find photos, more things to do, reviews, and more tourist information, use the Chatham trip maker website.

Chatham is just a stone's throw from Dennis. In July, daily temperatures in Chatham can reach 30°C, while at night they dip to 21°C. Finish up your sightseeing early on the 5th (Sun) so you can go by car to Provincetown.

Things to do in Chatham

Parks · Beaches · Outdoors · Museums

Side Trips

Provincetown

— 4 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.
Get some cultural insight at Wellfleet Bay Wildlife Sanctuary and Pilgrim Monument & Provincetown Museum. We've included these beaches for you: Herring Cove Beach and Long Point. There's much more to do: trek along Cape Cod Provincelands Trail, get a sense of history and politics at Provincetown Town Hall, explore the world behind art at Provincetown Art Association and Museum, and see what you can catch with a fishing tour.

To find photos, other places to visit, and more tourist information, use the Provincetown online trip itinerary planner.

You can drive from Chatham to Provincetown in an hour. Alternatively, you can take a bus. In July, daily temperatures in Provincetown can reach 30°C, while at night they dip to 20°C. Finish up your sightseeing early on the 9th (Thu) so you can travel to Nantucket.

Things to do in Provincetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Nantucket

— 5 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Step off the beaten path and head to Cisco Brewers and Sankaty Head Lighthouse. You'll enjoy a bit of beach vacationing at Madaket Beach and Jetties Beach. There's much more to do: enjoy the sand and surf at Siasconset Beach, visit a coastal fixture at Great Point Light, make a trip to Brant Point Lighthouse, and pause for some serene contemplation at St Paul's Episcopal Church.

To find reviews, traveler tips, other places to visit, and more tourist information, use the Nantucket trip planner.

Getting from Provincetown to Nantucket by combination of taxi and ferry takes about 3 hours. Other options: do a combination of bus and ferry. In July, daytime highs in Nantucket are 28°C, while nighttime lows are 20°C. Finish up your sightseeing early on the 14th (Tue) so you can travel back home.

Things to do in Nantucket

Beaches · Parks · Outdoors · 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.