60 days in Massachusetts Itinerary

60 days in Massachusetts Itinerary

Created using Inspirock Massachusetts 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
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 Martin Van Buren National Historic Site will appeal to history buffs. American Museum of Tort Law and Ozzie's Glass Gallery will appeal to museum buffs. Change things up with a short trip to Thomas Cole National Historic Site in Catskill (about 54 minutes away). The adventure continues: take in the awesome beauty at Monument Mountain, steep yourself in history at Chesterwood Museum, look for gifts at Williams & Sons Country Store, and take in nature's colorful creations at Naumkeag.

To plan Stockbridge vacation without wasting time, ask Inspirock to design an itinerary.

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. Traveling from Stockholm in June, you will find days in Stockbridge are a bit warmer (27°C), and nights are about the same (13°C). Finish your sightseeing early on the 5th (Fri) so you can 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. 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 Kaaterskill Falls (in Haines Falls), Eleanor Roosevelt National Historic Site (in Hyde Park) 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 Bennington Museum. Museum-lovers will get to explore Hancock Shaker Village 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 · Wildlife

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 Springfield Museums. Do some cultural sightseeing at Wadsworth Atheneum Museum of Art 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 · Wineries

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 Union Station 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 more to do: see the interesting displays at Museum of Russian Icons and get curious at EcoTarium.

For other places to visit, photos, ratings, and more tourist information, use the Worcester trip maker website.

Getting from Springfield to Worcester by car takes about an hour. Other options: take a bus; or take a train. In June in Worcester, expect temperatures between 28°C during the day and 15°C at night. Finish your sightseeing early on the 23rd (Tue) to allow enough 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.
Get some historical perspective at Chandler Hovey Park and Grace Episcopal Church. 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 Crane Beach (in Ipswich) and Gloucester (Good Harbor Beach & Cape Ann Museum). 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 contemplate the long history of The House of the Seven Gables.

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 · Wildlife

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 Strawbery Banke Museum. Step out of Boston to go to Ogunquit and see Marginal Way Walkway, which is approximately 1h 25 min away. There's still lots to do: contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, admire the masterpieces at Museum of Fine Arts, take an in-depth tour of Buckman Tavern, and appreciate the history behind The Mapparium.

To find more things to do, reviews, where to stay, and more tourist information, you can read our Boston trip app.

You can drive from Salem to Boston in an hour. Alternatively, you can take a train; or take a bus. June in Boston sees daily highs of 28°C and lows of 18°C at night. Wrap up your sightseeing on the 1st (Wed) early enough to drive 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 Mount Auburn Cemetery. You'll discover tucked-away gems like Boston Harbor Islands National Recreation Area and Nantasket Beach. Change things up with a short trip to DeCordova Sculpture Park & Museum in Lincoln (about 32 minutes away). There's still lots to do: witness the site of a historic battle at Lexington Green, examine the collection at Larz Anderson Auto Museum - Museum of Transportation, steep yourself in history at John F. Kennedy National Historic Site, and get engrossed in the history at Hancock-Clarke House.

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

Brookline is just a short distance from Boston. July in Brookline sees daily highs of 33°C and lows of 22°C at night. Cap off your sightseeing on the 5th (Sun) early enough to go by car 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), Battleship Cove (in Fall River) and Nobska Point Lighthouse (in Woods Hole). The adventure continues: take an in-depth tour of Pilgrim Hall Museum, immerse yourself in nature at National Monument to the Forefathers, examine the collection at Heritage Museums & Gardens, and browse the exhibits of Hedge House.

To see traveler tips, maps, more things to do, and other tourist information, go to the Plymouth day trip planning tool.

You can drive from Brookline to Plymouth in an hour. In July, daytime highs in Plymouth are 32°C, while nighttime lows are 20°C. Wrap up your sightseeing on the 9th (Thu) early enough to drive 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 First Encounter Beach. Explore the numerous day-trip ideas around Dennis: Eastham (Coast Guard Beach & Nauset Lighthouse). The adventure continues: stroll through Mayflower Beach, appreciate the extensive heritage of Fort Hill Rural Historic District, enjoy the sand and surf at West Dennis Beach, and stop by Stage Stop Candy.

Plan my trip to Dennis with suggested itineraries provided by Inspirock.

Traveling by car from Plymouth to Dennis takes an hour. Expect a daytime high around 31°C in July, and nighttime lows around 22°C. Finish your sightseeing early on the 13th (Mon) to allow enough time to drive to Chatham.

Things to do in Dennis

Beaches · Outdoors · Parks · 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, admire the masterpieces at Atwood Museum, and kick back and relax at Harding Beach.

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: look for all kinds of wild species at Beech Forest, Provincetown, cast your line with a fishing tour, ponder the world of politics at Provincetown Town Hall, and kick back and relax at Long Point.

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 Siasconset Beach. Museum-lovers will appreciate Egan Maritime's Nantucket Shipwreck & Lifesaving Museum and Nantucket Lightship Basket Museum. There's lots more to do: make a trip to Brant Point Lighthouse, enjoy the sand and surf at Cisco Beach, visit a coastal fixture at Sankaty Head 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 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.