56 days in Massachusetts Itinerary

56 days in Massachusetts Itinerary

Created using Inspirock Massachusetts tour planner

Make it your trip
Fly to Bradley International Airport, Drive to Stockbridge
1
Stockbridge
— 3 nights
Drive
2
Lenox
— 4 nights
Drive
3
Pittsfield
— 4 nights
Drive
4
Springfield
— 4 nights
Drive
5
Worcester
— 3 nights
Drive
6
Salem
— 4 nights
Drive
7
Boston
— 4 nights
Drive
8
Brookline
— 3 nights
Drive
9
Plymouth
— 6 nights
Drive
10
Dennis
— 4 nights
Drive
11
Chatham
— 4 nights
Drive
12
Provincetown
— 4 nights
Taxi to Hyannis, MA, Ferry to Nantucket
13
Nantucket
— 7 nights
Fly

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1

Stockbridge

— 3 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Olana State Historic Site and Chesterwood Museum are good opportunities to explore the local culture. Deepen your sense of the past at sights like National Shrine of the Divine Mercy and Martin Van Buren National Historic Site. Step out of Stockbridge to go to Winsted and see American Museum of Tort Law, which is approximately 52 minutes away. Next up on the itinerary: take your sightseeing to a higher altitude at Monument Mountain, look for gifts at Williams & Sons Country Store, take in nature's colorful creations at Naumkeag, and take in the exciting artwork at Ozzie's Glass Gallery.

To see photos, reviews, other places to visit, and tourist information, refer to the Stockbridge vacation builder website.

Stockholm, Sweden to Stockbridge is an approximately 22.5-hour combination of flight and car. The time zone difference moving from Central European Standard Time to Eastern Standard Time is minus 6 hours. When traveling from Stockholm in June, plan for somewhat warmer days in Stockbridge, with highs around 27°C, while nights are about the same with lows around 13°C. Wrap up your sightseeing on the 5th (Fri) early enough to drive to Lenox.

Things to do in Stockbridge

Historic Sites · Parks · Nature · Museums

Side Trips

Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Visit Vanderbilt Mansion National Historic Site and Eleanor Roosevelt National Historic Site for their historical value. You'll discover tucked-away gems like The Mount, Edith Wharton's Home and Old Rhinebeck Aerodrome. Get out of town with these interesting Lenox side-trips: Kaaterskill Falls (in Haines Falls) and Lighthouse (in Saugerties). There's still lots to do: browse the exhibits of Ventfort Hall Mansion and Gilded Age Museum and take a memorable drive along Concepts of Art Lenox Judaica.

Planning Lenox trip won't be overwhelming when you use Inspirock's itinerary maker.

Lenox is just a stone's throw from Stockbridge. In June, daily temperatures in Lenox can reach 27°C, while at night they dip to 13°C. Finish up your sightseeing early on the 9th (Tue) so you can go by car to Pittsfield.

Things to do in Lenox

Historic Sites · Museums · Nature · Parks

Side Trips

Pittsfield

— 4 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Appreciate the collections at MASS MoCA and Berkshire Museum. Get outdoors at Mount Greylock State Reservation and Lye Brook Falls. Explore Pittsfield's surroundings by going to Honora Winery & Vineyard (in Jacksonville), Robert Frost Stone House Museum (in Shaftsbury) and Bennington (Bennington Museum & The Old First Church). Next up on the itinerary: identify plant and animal life at Equinox Preservation Trust, steep yourself in history at Hancock Shaker Village, and admire the masterpieces at Williams College Museum of Art.

To see ratings, photos, where to stay, and tourist information, read Pittsfield journey builder app.

Pittsfield is very close to Lenox. In June in Pittsfield, expect temperatures between 27°C during the day and 13°C at night. Finish your sightseeing early on the 13th (Sat) to allow enough time to drive to Springfield.

Things to do in Pittsfield

Museums · Parks · Historic Sites · Nature

Side Trips

Springfield

— 4 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Get in touch with nature at Hammonasset Beach State Park and Norwottuck Rail Trail. Discover out-of-the-way places like Springfield Museums and Connecticut River Museum. Explore Springfield's surroundings by going to New Britain Museum of American Art (in New Britain), Wadsworth Atheneum Museum of Art (in Hartford) and Yankee Candle Flagship Store (in South Deerfield). The adventure continues: contemplate the long history of Springfield Armory National Historic Site, try to win big at MGM Springfield, and appreciate the history behind Dr. Seuss National Memorial Sculpture Garden.

To find ratings, where to stay, more things to do, and other tourist information, you can read our Springfield trip maker website.

You can drive from Pittsfield to Springfield in 1.5 hours. Expect a daytime high around 30°C in June, and nighttime lows around 14°C. Wrap up your sightseeing on the 17th (Wed) to allow time to drive to Worcester.

Things to do in Springfield

Museums · Parks · Childrens Museums · Outdoors

Side Trips

Worcester

— 3 nights
Worcester is a city and the county seat of Worcester County, Massachusetts, United States. Appreciate the collections at Worcester Art Museum and EcoTarium. Escape the urban bustle at Purgatory Chasm State Reservation and Monadnock State Park. You'll find plenty of places to visit near Worcester: Taylor Brooke Winery (in Woodstock) and Cathedral of the Pines (in Rindge). The adventure continues: see the interesting displays at Museum of Russian Icons.

Quickly create a custom-made itinerary for Worcester using our trip planner.

Traveling by car from Springfield to Worcester takes an hour. Alternatively, you can take a bus; or take a train. In June in Worcester, expect temperatures between 28°C during the day and 15°C at night. Wrap up your sightseeing on the 20th (Sat) to allow time to drive to Salem.

Things to do in Worcester

Museums · Nature · Parks · Childrens Museums

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.
Let the collections at Count Orlok's Nightmare Gallery and Phillips House capture your imagination. Your itinerary includes some good beach time at Good Harbor Beach and Crane Beach. Explore Salem's surroundings by going to Halibut Point State Park (in Rockport), Parker River National Wildlife Refuge (in Newburyport) and Cape Ann Museum (in Gloucester). There's much more to do: stop by Crow Haven Corner, steep yourself in history at The House of the Seven Gables, explore the galleries of Gedney House, and contemplate in the serene atmosphere at Grace Episcopal Church.

For other places to visit, reviews, photos, and more tourist information, go to the Salem trip itinerary tool.

You can drive from Worcester to Salem in 1.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of bus and train. June in Salem sees daily highs of 28°C and lows of 15°C at night. Finish your sightseeing early on the 24th (Wed) to allow enough time to drive to Boston.

Things to do in Salem

Parks · Museums · Historic Sites · Nature

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.
Do some cultural sightseeing at Museum of Fine Arts and Old State House. John F. Kennedy Presidential Museum & Library and RISD Museum will appeal to museum buffs. Explore Boston's surroundings by going to Concord (Louisa May Alcott's Orchard House & Minuteman National Park - Old North Bridge). There's still lots to do: admire the landmark architecture of Trinity Church, stroll through Adams National Historical Park, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, and stop by North End.

For more things to do, traveler tips, where to stay, and tourist information, read Boston journey planner.

You can drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. Expect a daytime high around 28°C in June, and nighttime lows around 18°C. Finish up your sightseeing early on the 28th (Sun) so you can go by car to Brookline.

Things to do in Boston

Museums · Historic Sites · Neighborhoods · Nature

Side Trips

Brookline

— 3 nights
Brookline is a town in Norfolk County, Massachusetts, in the United States, and is a part of Greater Boston. Step off the beaten path and head to The Harvard Museum of Natural History and DeCordova Sculpture Park & Museum. Let the collections at Hancock-Clarke House and The Plumbing Museum capture your imagination. Explore Brookline's surroundings by going to Hull (Nantasket Beach & Boston Harbor Islands National Recreation Area). Next up on the itinerary: explore the different monuments and memorials at Mount Auburn Cemetery and examine the collection at Larz Anderson Auto Museum - Museum of Transportation.

Before you visit Brookline, use our trip planner to discover what you can do and see there.

Brookline is just a stone's throw from Boston. In June, daytime highs in Brookline are 28°C, while nighttime lows are 18°C. Wrap up your sightseeing on the 1st (Wed) early enough to drive to Plymouth.

Things to do in Brookline

Museums · Parks · Nature · Historic Sites

Side Trips

Plymouth

— 6 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.
Discover out-of-the-way places like Lizzie Borden House and National Monument to the Forefathers. Your inner history buff will appreciate Mayflower II and Nobska Point Lighthouse. Explore Plymouth's surroundings by going to New Bedford Whaling Museum (in New Bedford), Battleship Cove (in Fall River) and Mashpee Commons (in Mashpee). There's lots more to do: stroll the grounds of Burial Hill, get curious at Sandwich Glass Museum, get engrossed in the history at Plimoth Patuxet, and steep yourself in history at Hoxie House.

To find traveler tips, ratings, other places to visit, and tourist information, go to the Plymouth road trip website.

Getting from Brookline to Plymouth by car takes about an hour. In July, daily temperatures in Plymouth can reach 32°C, while at night they dip to 20°C. Finish up your sightseeing early on the 7th (Tue) so you can go by car to Dennis.

Things to do in Plymouth

Museums · Historic Sites · Parks · Outdoors

Side Trips

Dennis

— 4 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. For shopping fun, head to Stage Stop Candy or Addison Art Gallery. Museum-lovers will appreciate Edward Gorey House and Salt Pond Visitor Center. Change things up with a short trip to Coast Guard Beach in Eastham (about 32 minutes away). There's much more to do: kick back and relax at Skaket Beach, stroll through West Dennis Beach, appreciate the extensive heritage of Fort Hill Rural Historic District, and contemplate the long history of Doane Rock.

For other places to visit, traveler tips, more things to do, and more tourist information, go to the Dennis tour itinerary builder.

Getting from Plymouth to Dennis by car takes about an hour. In July, plan for daily highs up to 31°C, and evening lows to 22°C. Finish your sightseeing early on the 11th (Sat) so you can drive to Chatham.

Things to do in Dennis

Beaches · Parks · Outdoors · Historic Sites

Side Trips

Chatham

— 4 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. Let the collections at Chatham Marconi Maritime Center and Maps of Antiquity capture your imagination. Your cultural itinerary includes sights like Chatham Lighthouse and Chatham's Godfrey Windmill. The adventure continues: look for all kinds of wild species at Monomoy National Wildlife Refuge, kick back and relax at Nauset Beach, tour the pleasant surroundings at Ridgevale Beach, and explore the world behind art at Atwood Museum.

Plan trip to Chatham with our itinerary maker to find out where to go and what to do.

Chatham is just a short distance from Dennis. In July, daily temperatures in Chatham can reach 30°C, while at night they dip to 21°C. Cap off your sightseeing on the 15th (Wed) early enough to go by car to Provincetown.

Things to do in Chatham

Parks · Beaches · Outdoors · Historic Sites

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.
Wellfleet Bay Wildlife Sanctuary and Provincetown Town Hall are good opportunities to explore the local culture. Take a break from the city and head to Herring Cove Beach and Cape Cod Provincelands Trail. And it doesn't end there: kick back and relax at Long Point, browse the exhibits of Pilgrim Monument & Provincetown Museum, tour the pleasant surroundings at Marconi Beach, and take a memorable tour with Tours.

To see ratings, where to stay, maps, and more tourist information, use the Provincetown attractions planner.

Drive from Chatham to Provincetown in an hour. Alternatively, you can take a bus. In July, daytime highs in Provincetown are 30°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 19th (Sun) to allow time to travel to Nantucket.

Things to do in Provincetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Nantucket

— 7 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Deepen your sense of the past at sights like Brant Point Lighthouse and Great Point Light. You'll get in some beach time at Madaket Beach and Siasconset Beach. There's still lots to do: enjoy the sea views from Sankaty Head Lighthouse, kick back and relax at Jetties Beach, sample the fine beverages at Cisco Brewers, and take in the architecture and atmosphere at Nantucket United Methodist Church.

To find reviews, photos, ratings, and tourist information, use the Nantucket trip 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, plan for daily highs up to 28°C, and evening lows to 20°C. Wrap up your sightseeing on the 26th (Sun) early enough 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.