60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts sightseeing planner

Make it your trip
Fly to Bradley International Airport, Drive to Stockbridge
1
Stockbridge
— 4 nights
Drive
2
Lenox
— 4 nights
Drive
3
Pittsfield
— 4 nights
Drive
4
Northampton
— 3 nights
Drive
5
Amherst
— 3 nights
Drive
6
Springfield
— 4 nights
Drive
7
Worcester
— 4 nights
Drive
8
Salem
— 4 nights
Drive
9
Boston
— 4 nights
Drive
10
Brookline
— 4 nights
Drive
11
Plymouth
— 4 nights
Drive
12
Barnstable
— 2 nights
Drive
13
Dennis
— 6 nights
Drive
14
Chatham
— 8 nights
Drive to General Edward Lawrence Logan International Airport, Fly to Stockholm-Arlanda Airport

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1

Stockbridge

— 4 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Eschew the tourist crowds and head to Naumkeag and Martin Van Buren National Historic Site. Get some historical perspective at National Shrine of the Divine Mercy and Thomas Cole National Historic Site. Change things up with these side-trips from Stockbridge: White Memorial Conservation Center (in Litchfield) and American Museum of Tort Law (in Winsted). Next up on the itinerary: take in the awesome beauty at Monument Mountain, look for gifts at Williams & Sons Country Store, admire the masterpieces at Norman Rockwell Museum, and contemplate the long history of Chesterwood Museum.

To see reviews, photos, maps, and more tourist information, read Stockbridge trip planner.

Stockholm, Sweden to Stockbridge is an approximately 22.5-hour combination of flight and car. Due to the time zone difference, you'll gain 6 hours traveling from Stockholm to Stockbridge. Expect a bit warmer weather when traveling from Stockholm in June: highs in Stockbridge hover around 27°C, while lows dip to 13°C. Wrap up your sightseeing on the 6th (Sat) to allow time to drive to Lenox.

Things to do in Stockbridge

Historic Sites · Parks · Museums · Wildlife

Side Trips

Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. Your cultural itinerary includes sights like Vanderbilt Mansion National Historic Site and Ventfort Hall Mansion and Gilded Age Museum. You'll explore and learn at Storm King Art Center and The Mount, Edith Wharton's Home. Venture out of the city with trips to Benmarl Vineyards and Winery (in Marlboro), Eleanor Roosevelt National Historic Site (in Hyde Park) and Kaaterskill Falls (in Haines Falls). There's still lots to do: enjoy the sea views from Lighthouse and stop by Concepts of Art Lenox Judaica.

To find maps, other places to visit, more things to do, and more tourist information, refer to the Lenox online tour itinerary builder.

Lenox is just a short distance from Stockbridge. In June in Lenox, expect temperatures between 27°C during the day and 13°C at night. Wrap up your sightseeing on the 10th (Wed) to allow time to drive 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 in touch with nature at Mount Greylock State Reservation and Ashuwillticook Rail Trail. Step off the beaten path and head to MASS MoCA and Lye Brook Falls. Change things up with these side-trips from Pittsfield: Bennington (The Old First Church & Bennington Museum), Robert Frost Stone House Museum (in Shaftsbury) and Williams College Museum of Art (in Williamstown). There's lots more to do: contemplate the long history of Herman Melville's Arrowhead, examine the collection at Berkshire Museum, experience rural life at Hancock Shaker Village, and learn about winemaking at Balderdash Cellars.

To see reviews, other places to visit, maps, and more tourist information, read our Pittsfield trip planner.

Pittsfield is very close to Lenox. In June, plan for daily highs up to 27°C, and evening lows to 13°C. Wrap up your sightseeing on the 14th (Sun) to allow time to drive to Northampton.

Things to do in Pittsfield

Museums · Historic Sites · Parks · Nature

Side Trips

Northampton

— 3 nights
The city of Northampton is the county seat of Hampshire County, Massachusetts, United States. Historic Deerfield and Memorial Hall Museum are good opportunities to explore the local culture. You'll explore and learn at Smith College Museum of Art and Historic Northampton. You'll find plenty of places to visit near Northampton: Creamery Covered Bridge (in Brattleboro) and Honora Winery & Vineyard (in Jacksonville). The adventure continues: explore the landscape on two wheels at Norwottuck Rail Trail, take in nature's colorful creations at Magic Wings Butterfly Conservatory and Gardens, and examine the collection at Yankee Candle Flagship Store.

Ask Inspirock to suggest an itinerary and make planning a trip to Northampton fast, fun, and easy.

You can drive from Pittsfield to Northampton in 1.5 hours. Expect a daytime high around 30°C in June, and nighttime lows around 14°C. Cap off your sightseeing on the 17th (Wed) early enough to go by car to Amherst.

Things to do in Northampton

Museums · Historic Sites · Parks · Shopping

Side Trips

Amherst

— 3 nights
Amherst is a town in Hampshire County, Massachusetts, United States, in the Connecticut River valley. You'll explore and learn at Emily Dickinson Museum and Yiddish Book Center. Get a sense of the local culture at Eric Carle Museum of Picture Book Art and Amherst College Museum of Natural History. When in Amherst, make a side trip to see Monadnock State Park in Jaffrey, approximately Jaffrey away. Next up on the itinerary: explore the world behind art at Mead Art Museum and identify plant and animal life at New England Falconry.

For more things to do, maps, where to stay, and tourist information, refer to the Amherst route builder website.

Amherst is very close to Northampton. In June, daytime highs in Amherst are 30°C, while nighttime lows are 14°C. Wrap up your sightseeing on the 20th (Sat) to allow time to drive to Springfield.

Things to do in Amherst

Museums · Parks · Wildlife · Nature

Side Trips

Springfield

— 4 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Museum-lovers will get to explore Yale University Art Gallery and Springfield Museums. Get a sense of the local culture at Wadsworth Atheneum Museum of Art and Springfield Armory National Historic Site. You'll find plenty of places to visit near Springfield: Yale Peabody Museum of Natural History (in New Haven) and Hammonasset Beach State Park (in Madison). And it doesn't end there: see the interesting displays at New England Air Museum, appreciate the history behind Dr. Seuss National Memorial Sculpture Garden, try to win big at MGM Springfield, and explore the activities along Watershops Pond.

For photos, maps, reviews, and more tourist information, read our Springfield route planner.

Drive from Amherst to Springfield in an hour. In June in Springfield, expect temperatures between 30°C during the day and 14°C at night. Wrap up your sightseeing on the 24th (Wed) to allow time to drive to Worcester.

Things to do in Springfield

Museums · Childrens Museums · Parks · Nature

Side Trips

Worcester

— 4 nights
Worcester is a city and the county seat of Worcester County, Massachusetts, United States. Museum-lovers will appreciate Worcester Art Museum and EcoTarium. Step out of the city life by going to Purgatory Chasm State Reservation and Green Hill Park. Change things up with these side-trips from Worcester: Wrentham Village Premium Outlets (in Wrentham) and Cathedral of the Pines (in Rindge). The adventure continues: examine the collection at Museum of Russian Icons, do a tasting at Nashoba Valley Winery, and admire the striking features of Union Station.

Plan my Worcester trip by asking Inspirock to come up with tips and suggestions.

Traveling by car from Springfield to Worcester takes an hour. Alternatively, you can take a bus; or take a train. Expect a daytime high around 28°C in June, and nighttime lows around 15°C. Wrap up your sightseeing on the 28th (Sun) early enough to drive to Salem.

Things to do in Worcester

Museums · Childrens Museums · Wildlife · Parks

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.
Museum-lovers will appreciate Count Orlok's Nightmare Gallery and Cape Ann Museum. Your inner history buff will appreciate The Custom House and The House of the Seven Gables. Explore Salem's surroundings by going to Good Harbor Beach (in Gloucester) and Crane Beach (in Ipswich). And it doesn't end there: look for gifts at Crow Haven Corner, admire the striking features of Phillips House, enjoy the sea views from Chandler Hovey Park, and contemplate in the serene atmosphere at Grace Episcopal Church.

To find photos, ratings, other places to visit, and other tourist information, go to the Salem trip itinerary builder app.

Getting from Worcester to Salem by car takes about 1.5 hours. Other options: do a combination of bus and train; or do a combination of bus and train. In June, plan for daily highs up to 28°C, and evening lows to 15°C. Finish your sightseeing early on the 2nd (Thu) to allow enough time to drive to Boston.

Things to do in Salem

Museums · Historic Sites · Beaches · Parks

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.
Freedom Trail and Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill will appeal to history buffs. You'll discover tucked-away gems like Old State House and Harvard Art Museums. There's much more to do: head off the coast to Castle Island, explore the world behind art at Museum of Fine Arts, enjoy breathtaking views from Skywalk Observatory, and contemplate in the serene atmosphere at Trinity Church.

To see photos, more things to do, other places to visit, and other tourist information, you can read our Boston road trip planning site.

Traveling by car from Salem to Boston takes an hour. Alternatively, you can take a train; or take a bus. Expect a daytime high around 33°C in July, and nighttime lows around 22°C. Finish your sightseeing early on the 6th (Mon) so you can drive to Brookline.

Things to do in Boston

Museums · Historic Sites · Parks · Nature

Side Trip

Brookline

— 4 nights
Brookline is a town in Norfolk County, Massachusetts, in the United States, and is a part of Greater Boston. Deepen your sense of the past at sights like Mount Auburn Cemetery and Hancock-Clarke House. Get some cultural insight at The Harvard Museum of Natural History and The Plumbing Museum. Explore Brookline's surroundings by going to The Butterfly Place (in Westford), Hull (Nantasket Beach & Boston Harbor Islands National Recreation Area) and DeCordova Sculpture Park & Museum (in Lincoln). The adventure continues: steep yourself in history at John F. Kennedy National Historic Site and see the interesting displays at Larz Anderson Auto Museum - Museum of Transportation.

For where to stay, other places to visit, more things to do, and other tourist information, read our Brookline trip itinerary maker app.

Brookline is just a stone's throw from Boston. In July, daily temperatures in Brookline can reach 33°C, while at night they dip to 22°C. Cap off your sightseeing on the 10th (Fri) early enough to go by car to Plymouth.

Things to do in Brookline

Museums · Parks · Historic Sites · Nature

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.
Visiting National Monument to the Forefathers and Shining Sea Bikeway will get you outdoors. Mayflower II and Burial Hill will appeal to history buffs. Step out of Plymouth to go to East Sandwich and see Green Briar Nature Center and Jam Kitchen, which is approximately 30 minutes away. Next up on the itinerary: get engrossed in the history at Pilgrim Hall Museum, get lost in a book at Mayflower Society House and Library, appreciate the history behind Plymouth Rock, and see the interesting displays at Heritage Museums & Gardens.

For more things to do, other places to visit, traveler tips, and more tourist information, go to the Plymouth trip itinerary maker app.

Traveling by car from Brookline to Plymouth takes an hour. In July in Plymouth, expect temperatures between 32°C during the day and 20°C at night. Finish up your sightseeing early on the 14th (Tue) so you can go by car to Barnstable.

Things to do in Plymouth

Museums · Historic Sites · Parks · Wildlife

Side Trips

Barnstable

— 2 nights
Barnstable is a city, referred to as the Town of Barnstable, in the U.S. state of Massachusetts and the county seat of Barnstable County. Kick off your visit on the 15th (Wed): see the interesting displays at Cahoon Museum of American Art, then stop by Mashpee Commons, then steep yourself in history at Captain Bangs Hallet House Museum, and finally view the masterpieces at Samuell Day Gallery. On the 16th (Thu), you'll have a packed day of sightseeing: kick back and relax at Craigville Beach, examine the collection at Coast Guard Heritage Museum, and then identify plant and animal life at Long Pasture Wildlife Sanctuary.

To see other places to visit, more things to do, and tourist information, go to the Barnstable online itinerary planner.

Traveling by car from Plymouth to Barnstable takes an hour. July in Barnstable sees daily highs of 31°C and lows of 22°C at night. Finish up your sightseeing early on the 16th (Thu) so you can go by car to Dennis.

Things to do in Barnstable

Museums · Parks · Wildlife · Beaches

Side Trips

Dennis

— 6 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Do some cultural sightseeing at Wellfleet Bay Wildlife Sanctuary and Provincetown Town Hall. You'll discover tucked-away gems like Skaket Beach and Herring Cove Beach. Explore Dennis' surroundings by going to Eastham (Coast Guard Beach & Nauset Light Beach), Provincetown (Cape Cod Provincelands Trail, Provincetown Library, &more) and Marconi Beach (in Wellfleet). There's lots more to do: stroll through Mayflower Beach, steep yourself in history at Doane Rock, kick back and relax at First Encounter Beach, and pause for some serene contemplation at Church of the Transfiguration.

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

Dennis is very close to Barnstable. Expect a daytime high around 31°C in July, and nighttime lows around 22°C. Finish your sightseeing early on the 22nd (Wed) so you can drive to Chatham.

Things to do in Dennis

Parks · Outdoors · Beaches · Historic Sites

Side Trips

Chatham

— 8 nights
Chatham is a town in Barnstable County, Massachusetts, United States, Barnstable County being coextensive with Cape Cod. You'll explore and learn at Chatham Marconi Maritime Center and Shark Center. Step out of the city life by going to Nauset Beach and Harding Beach. The adventure continues: visit a coastal fixture at Chatham Lighthouse, shop like a local with Chatham Pier and Fish Market, explore the world behind art at Atwood Museum, and kick back and relax at Oyster Pond.

To find ratings, more things to do, maps, and tourist information, read Chatham trip itinerary planning website.

Chatham is very close to Dennis. In July, plan for daily highs up to 30°C, and evening lows to 21°C. Wrap up your sightseeing on the 30th (Thu) to allow time to travel back home.

Things to do in Chatham

Parks · Outdoors · Beaches · Historic Sites

Side Trips

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.