60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts planner

Make it your trip
Fly to Theodore Francis Green State Airport, Drive to Stockbridge
1
Stockbridge
— 3 nights
Drive
2
Lenox
— 4 nights
Drive
3
Pittsfield
— 4 nights
Drive
4
Northampton
— 3 nights
Drive
5
Springfield
— 4 nights
Drive
6
Worcester
— 3 nights
Drive
7
Salem
— 4 nights
Drive
8
Boston
— 4 nights
Drive
9
Brookline
— 4 nights
Drive
10
Plymouth
— 4 nights
Drive
11
Dennis
— 4 nights
Drive
12
Chatham
— 4 nights
Drive
13
Provincetown
— 6 nights
Taxi to Hyannis, MA, Ferry to Nantucket
14
Nantucket
— 7 nights
Fly

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1

Stockbridge

— 3 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. National Shrine of the Divine Mercy and Chesterwood Museum will appeal to history buffs. American Museum of Tort Law and Ozzie's Glass Gallery will appeal to museum buffs. Venture out of the city with trips to Martin Van Buren National Historic Site (in Kinderhook) and Thomas Cole National Historic Site (in Catskill). There's much more to do: take in the awesome beauty at Monument Mountain, stop by Williams & Sons Country Store, and take in nature's colorful creations at Naumkeag.

To see where to stay, photos, maps, and tourist information, go to the Stockbridge trip itinerary planner.

Stockholm, Sweden to Stockbridge is an approximately 19-hour combination of flight and car. Due to the time zone difference, you'll gain 6 hours traveling from Stockholm to Stockbridge. When traveling from Stockholm in June, plan for somewhat warmer days and about the same nights in Stockbridge: temperatures range from 27°C by day to 13°C at night. Wrap up your sightseeing on the 5th (Fri) early enough to drive to Lenox.

Things to do in Stockbridge

Historic Sites · Parks · Nature · Shopping

Side Trips

Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. You'll explore and learn at Storm King Art Center and The Mount, Edith Wharton's Home. Satisfy your inner culture vulture at Vanderbilt Mansion National Historic Site and Lighthouse. Venture out of the city with trips to Eleanor Roosevelt National Historic Site (in Hyde Park), Kaaterskill Falls (in Haines Falls) and Angry Orchard (in Walden). There's more to do: admire the striking features of Ventfort Hall Mansion and Gilded Age Museum and look for gifts at Concepts of Art Lenox Judaica.

For photos, maps, traveler tips, and more tourist information, refer to the Lenox tour planning website.

Lenox is just a stone's throw from Stockbridge. Expect a daytime high around 27°C in June, and nighttime lows around 13°C. Wrap up your sightseeing on the 9th (Tue) early enough 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. You'll discover tucked-away gems like MASS MoCA and Hancock Shaker Village. Museum-lovers will get to explore Bennington Museum and Berkshire Museum. You'll find plenty of places to visit near Pittsfield: Manchester (Equinox Preservation Trust & Lye Brook Falls), Robert Frost Stone House Museum (in Shaftsbury) and The Old First Church (in Bennington). There's more to do: admire the majestic nature at Mount Greylock State Reservation.

Take the guesswork out of planning a Pittsfield vacation by using our trip itinerary maker.

Pittsfield is very close to Lenox. In June, daytime highs in Pittsfield are 27°C, while nighttime lows are 13°C. Wrap up your sightseeing on the 13th (Sat) to allow time to drive to Northampton.

Things to do in Pittsfield

Museums · Parks · Historic Sites · Nature

Side Trips

Northampton

— 3 nights
The city of Northampton is the county seat of Hampshire County, Massachusetts, United States. You'll explore and learn at Historic Deerfield and Yankee Candle Flagship Store. Satisfy your inner culture vulture at Smith College Museum of Art and Eric Carle Museum of Picture Book Art. Go for a jaunt from Northampton to Brattleboro to see Creamery Covered Bridge about 50 minutes away. There's much more to do: explore the landscape on two wheels at Norwottuck Rail Trail, look for all kinds of wild species at New England Falconry, and take in nature's colorful creations at Magic Wings Butterfly Conservatory and Gardens.

To find other places to visit, ratings, and tourist information, read Northampton trip planner.

You can drive from Pittsfield to Northampton in 1.5 hours. In June, daily temperatures in Northampton can reach 30°C, while at night they dip to 14°C. Finish your sightseeing early on the 16th (Tue) to allow enough time to drive to Springfield.

Things to do in Northampton

Museums · Parks · Wildlife · Shopping

Side Trips

Springfield

— 4 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Explore hidden gems such as Yale University Art Gallery and Wadsworth Atheneum Museum of Art. Do some cultural sightseeing at Springfield Museums and Dinosaur State Park. You'll find plenty of places to visit near Springfield: Yale Center for British Art (in New Haven) and Brignole Vineyards (in East Granby). Next up on the itinerary: brush up on your military savvy at Springfield Armory National Historic Site, make a trip to Dr. Seuss National Memorial Sculpture Garden, appreciate the history behind William Pynchon Statue, and try your luck at MGM Springfield.

For photos, where to stay, reviews, and tourist information, refer to the Springfield day trip website.

Springfield is very close to Northampton. In June in Springfield, expect temperatures between 30°C during the day and 14°C at night. Finish your sightseeing early on the 20th (Sat) so you can drive to Worcester.

Things to do in Springfield

Museums · Childrens Museums · Historic Sites · Fun & Games

Side Trips

Worcester

— 3 nights
Worcester is a city and the county seat of Worcester County, Massachusetts, United States. Visiting Purgatory Chasm State Reservation and Monadnock State Park will get you outdoors. Worcester Art Museum and Museum of Russian Icons are good opportunities to explore the local culture. Step out of Worcester with an excursion to Cathedral of the Pines in Rindge--about 1h 5 min away. There's still lots to do: get curious at EcoTarium and make a trip to Union Station.

For photos, where to stay, maps, and more tourist information, read Worcester route tool.

Traveling by car from Springfield to Worcester takes an hour. Alternatively, you can take a bus; or take a train. In June, daytime highs in Worcester are 28°C, while nighttime lows are 15°C. Cap off your sightseeing on the 23rd (Tue) early enough to go by car 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.
Get some historical perspective at Chandler Hovey Park and The House of the Seven Gables. Discover out-of-the-way places like Halibut Point State Park and Parker River National Wildlife Refuge. Venture out of the city with trips to Gloucester (Good Harbor Beach & Cape Ann Museum) and Crane Beach (in Ipswich). There's lots more to do: explore the world behind art at Count Orlok's Nightmare Gallery, enjoy the sea views from Derby Wharf Light Station, explore the galleries of Gedney House, and admire the striking features of Phillips House.

To find traveler tips, maps, more things to do, and more tourist information, use the Salem online vacation planner.

Traveling by car from Worcester to Salem takes 1.5 hours. Alternatively, you can do a combination of bus and train; or do a combination of bus and train. Expect a daytime high around 28°C in June, and nighttime lows around 15°C. Wrap up your sightseeing on the 27th (Sat) to allow 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.
Step off the beaten path and head to Old State House and Trinity Church. Deepen your sense of the past at sights like Freedom Trail and Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill. Explore Boston's surroundings by going to Marginal Way Walkway (in Ogunquit) and Strawbery Banke Museum (in Portsmouth). There's lots more to do: get a sense of history and politics at Massachusetts State House, steep yourself in history at Buckman Tavern, appreciate the history behind The Mapparium, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

To see traveler tips, other places to visit, where to stay, and other tourist information, you can read our Boston travel itinerary planner.

Drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. In June, daily temperatures in Boston can reach 28°C, while at night they dip to 18°C. Finish up your sightseeing early on the 1st (Wed) so you can go by car to Brookline.

Things to do in Boston

Historic Sites · Museums · Neighborhoods · Shopping

Side Trips

Brookline

— 4 nights
Brookline is a town in Norfolk County, Massachusetts, in the United States, and is a part of Greater Boston. Get some cultural insight at The Harvard Museum of Natural History and Lexington Green. You'll discover tucked-away gems like Mount Auburn Cemetery and Nantasket Beach. Venture out of the city with trips to Boston Harbor Islands National Recreation Area (in Hull) and DeCordova Sculpture Park & Museum (in Lincoln). There's still lots to do: contemplate the long history of Hancock-Clarke House and examine the collection at Larz Anderson Auto Museum - Museum of Transportation.

To find where to stay, more things to do, ratings, and other tourist information, you can read our Brookline vacation planner.

Brookline is just a short distance from Boston. In July in Brookline, expect temperatures between 33°C during the day and 22°C at night. Finish your sightseeing early on the 5th (Sun) so you can drive to Plymouth.

Things to do in Brookline

Museums · Historic Sites · Parks · 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.
Visit Lizzie Borden House and Mayflower II for their historical value. Plimoth Patuxet and The Jenney are good opportunities to explore the local culture. Change things up with these side-trips from Plymouth: New Bedford Whaling Museum (in New Bedford), Nobska Point Lighthouse (in Woods Hole) and Battleship Cove (in Fall River). The adventure continues: pause for some photo ops at National Monument to the Forefathers, examine the collection at Heritage Museums & Gardens, browse the exhibits of Hedge House, and take an in-depth tour of Pilgrim Hall Museum.

For other places to visit, photos, and tourist information, use the Plymouth holiday maker website.

Getting from Brookline to Plymouth by car takes about an hour. In July, plan for daily highs up to 32°C, and evening lows to 20°C. Cap off your sightseeing on the 9th (Thu) early enough to go by car to Dennis.

Things to do in Plymouth

Museums · Historic Sites · Nature · Parks

Side Trips

Dennis

— 4 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Museum-lovers will get to explore Edward Gorey House and Salt Pond Visitor Center. Discover out-of-the-way places like Skaket Beach and Mayflower Beach. Explore the numerous day-trip ideas around Dennis: Eastham (Coast Guard Beach & Nauset Lighthouse). Next up on the itinerary: explore and take pictures at First Encounter Beach, get to know the fascinating history of Fort Hill Rural Historic District, stroll through West Dennis Beach, and kick back and relax at Seagull Beach.

To see ratings, reviews, more things to do, and other tourist information, go to the Dennis trip planner.

Traveling by car from Plymouth to Dennis takes an hour. In July in Dennis, expect temperatures between 31°C during the day and 22°C at night. Finish up your sightseeing early on the 13th (Mon) so you can go by car to Chatham.

Things to do in Dennis

Parks · Beaches · 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. We've included these beaches for you: Nauset Beach and Chatham Lighthouse Beach. Discover out-of-the-way places like Chatham Lighthouse and Monomoy National Wildlife Refuge. There's lots more to do: get curious at Chatham Marconi Maritime Center, admire the majestic nature at Nickerson State Park, kick back and relax at Harding Beach, and pick up a one of a kind souvenir at Maps of Antiquity.

To see traveler tips, photos, ratings, and more tourist information, read Chatham travel planning website.

Chatham is just a short distance from Dennis. Expect a daytime high around 30°C in July, and nighttime lows around 21°C. Finish your sightseeing early on the 17th (Fri) so you can drive to Provincetown.

Things to do in Chatham

Parks · Beaches · Outdoors · Historic Sites

Side Trips

Provincetown

— 6 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.
Your inner history buff will appreciate Wellfleet Bay Wildlife Sanctuary and Highland Light. Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum will appeal to museum buffs. There's still lots to do: stroll through Cape Cod Provincelands Trail, cast your line with a fishing tour, ponder the world of politics at Provincetown Town Hall, and take a peaceful walk through Beech Forest, Provincetown.

To find maps, reviews, photos, and more tourist information, go to the Provincetown visit planner.

You can drive from Chatham to Provincetown in an hour. Another option is to take a bus. In July, plan for daily highs up to 30°C, and evening lows to 20°C. Wrap up your sightseeing on the 23rd (Thu) to allow time to travel to Nantucket.

Things to do in Provincetown

Parks · Outdoors · 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. Escape the urban bustle at Madaket Beach and Cisco Beach. Museum-lovers will appreciate Egan Maritime's Nantucket Shipwreck & Lifesaving Museum and Nantucket Lightship Basket Museum. There's lots more to do: tour the pleasant surroundings at Surfside Beach, enjoy the sand and surf at Jetties Beach, visit a coastal fixture at Brant Point Lighthouse, and take in the architecture and atmosphere at Nantucket United Methodist Church.

To see more things to do, ratings, traveler tips, and more tourist information, use the Nantucket route planner.

You can do a combination of taxi and ferry from Provincetown to Nantucket in 3 hours. Alternatively, you can do a combination of bus and ferry. In July, daytime highs in Nantucket are 28°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 30th (Thu) early enough to fly back home.

Things to do in Nantucket

Outdoors · Parks · Beaches · 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.