52 days in Massachusetts Itinerary

52 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip 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
— 6 nights
Drive
4
Springfield
— 4 nights
Drive
5
Worcester
— 3 nights
Drive
6
Salem
— 4 nights
Drive
7
Boston
— 4 nights
Drive
8
Plymouth
— 4 nights
Drive
9
Dennis
— 4 nights
Drive
10
Chatham
— 4 nights
Drive
11
Provincetown
— 4 nights
Taxi to Hyannis, MA, Ferry to Nantucket
12
Nantucket
— 6 nights
Fly

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Stockbridge

— 3 nights
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Take a break from the city and head to Monument Mountain and White Memorial Conservation Center. You'll explore and learn at American Museum of Tort Law and Ozzie's Glass Gallery. Go for a jaunt from Stockbridge to Kinderhook to see Martin Van Buren National Historic Site about 40 minutes away. There's lots more to do: take in the spiritual surroundings of National Shrine of the Divine Mercy, admire the natural beauty at Naumkeag, contemplate the long history of Chesterwood Museum, and stop by Williams & Sons Country Store.

For maps, ratings, reviews, and more tourist information, you can read our Stockbridge holiday builder site.

Stockholm, Sweden to Stockbridge 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 a bit warmer days and about the same nights in Stockbridge, ranging from highs of 27°C to lows of 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 · Wildlife

Side Trips

Lenox

— 4 nights
Lenox is an affluent town in Berkshire County, Massachusetts, United States. You'll discover tucked-away gems like Vanderbilt Mansion National Historic Site and Storm King Art Center. Visiting Kaaterskill Falls and Concepts of Art Lenox Judaica will get you outdoors. Explore the numerous day-trip ideas around Lenox: Lighthouse (in Saugerties), Eleanor Roosevelt National Historic Site (in Hyde Park) and Angry Orchard (in Walden). There's more to do: contemplate the long history of The Mount, Edith Wharton's Home and admire the landmark architecture of Ventfort Hall Mansion and Gilded Age Museum.

To see traveler tips, maps, where to stay, and other tourist information, read Lenox tour itinerary builder site.

Lenox is just a stone's throw from Stockbridge. In June, plan for daily highs up to 27°C, and evening lows 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 · Parks · Nature

Side Trips

Pittsfield

— 6 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Eschew the tourist crowds and head to MASS MoCA and Mount Greylock State Reservation. Hancock Shaker Village and Berkshire Museum are good opportunities to explore the local culture. You'll find plenty of places to visit near Pittsfield: Robert Frost Stone House Museum (in Shaftsbury), Manchester (Lye Brook Falls & Equinox Preservation Trust) and Honora Winery & Vineyard (in Jacksonville). There's still lots to do: explore the world behind art at Bennington Museum, get engrossed in the history at Herman Melville Memorial Room, steep yourself in history at Herman Melville's Arrowhead, and pick up a one of a kind souvenir at Tallulah's Antiques & More.

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

Pittsfield is just a stone's throw from Lenox. June in Pittsfield sees daily highs of 27°C and lows of 13°C at night. Finish your sightseeing early on the 15th (Mon) to allow enough time to drive to Springfield.

Things to do in Pittsfield

Museums · Parks · Historic Sites · Outdoors

Side Trips

Springfield

— 4 nights
Springfield is a city in western New England, and the seat of Hampden County, Massachusetts, United States. Step off the beaten path and head to Springfield Museums and Hammonasset Beach State Park. Do some cultural sightseeing at Wadsworth Atheneum Museum of Art and Springfield Armory National Historic Site. Change things up with these side-trips from Springfield: Yankee Candle Flagship Store (in South Deerfield), Brignole Vineyards (in East Granby) and Yale Peabody Museum of Natural History (in New Haven). There's much more to do: examine the collection at New England Air Museum, admire the natural beauty at Dr. Seuss National Memorial Sculpture Garden, explore the world behind art at Smith College Museum of Art, and try your luck at MGM Springfield.

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

Traveling by car from Pittsfield to Springfield takes 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 19th (Fri) so you can drive to Worcester.

Things to do in Springfield

Museums · Childrens Museums · Parks · Shopping

Side Trips

Worcester

— 3 nights
Worcester is a city and the county seat of Worcester County, Massachusetts, United States. Get a sense of the local culture at Worcester Art Museum and Union Station. Get in touch with nature at Purgatory Chasm State Reservation and Monadnock State Park. Change things up with a short trip to Cathedral of the Pines in Rindge (about 1h 5 min away). There's more to do: examine the collection at Museum of Russian Icons and learn about winemaking at Nashoba Valley Winery.

For other places to visit, traveler tips, photos, and other tourist information, you can read our Worcester online trip itinerary planner.

Traveling by car from Springfield to Worcester takes an hour. Alternatively, you can take a bus; or take a train. In June, plan for daily highs up to 28°C, and evening lows to 15°C. Cap off your sightseeing on the 22nd (Mon) early enough to go by car to Salem.

Things to do in Worcester

Museums · Nature · Parks · Wineries

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.
You'll discover tucked-away gems like Halibut Point State Park and Cape Ann Museum. You'll explore and learn at Count Orlok's Nightmare Gallery and Phillips House. Venture out of the city with trips to Parker River National Wildlife Refuge (in Newburyport), Good Harbor Beach (in Gloucester) and Crane Beach (in Ipswich). Next up on the itinerary: look for gifts at Crow Haven Corner, take in the architecture and atmosphere at Grace Episcopal Church, enjoy the sea views from Chandler Hovey Park, and make a trip to Derby Wharf Light Station.

To see reviews, traveler tips, other places to visit, and other tourist information, you can read our Salem trip planner.

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. In June in Salem, expect temperatures between 28°C during the day and 15°C at night. Cap off your sightseeing on the 26th (Fri) early enough to go by car 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.
Deepen your sense of the past at sights like Freedom Trail and Trinity Church. Museum of Fine Arts and Old State House will appeal to museum buffs. Explore the numerous day-trip ideas around Boston: Marginal Way Walkway (in Ogunquit), DeCordova Sculpture Park & Museum (in Lincoln) and Strawbery Banke Museum (in Portsmouth). There's lots more to do: contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, get engrossed in the history at John F. Kennedy Presidential Museum & Library, admire the masterpieces at Harvard Art Museums, and pause for some photo ops at The Mapparium.

For where to stay, maps, other places to visit, and more tourist information, you can read our Boston trip 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. Cap off your sightseeing on the 30th (Tue) early enough to go by car to Plymouth.

Things to do in Boston

Museums · Historic Sites

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 Dolphin & Whale Watching will get you outdoors. Museum-lovers will get to explore Lizzie Borden House and New Bedford Whaling Museum. Get out of town with these interesting Plymouth side-trips: Nobska Point Lighthouse (in Woods Hole), Cape Cod Canal (in Buzzards Bay) and Shining Sea Bikeway (in Falmouth). There's still lots to do: take an in-depth tour of Pilgrim Hall Museum, contemplate the long history of Dexter’s Grist Mill, and see the interesting displays at Heritage Museums & Gardens.

To see ratings, maps, more things to do, and other tourist information, read our Plymouth itinerary app.

Drive from Boston to Plymouth in an hour. Alternatively, you can take a train; or take a bus. June in Plymouth sees daily highs of 28°C and lows of 15°C at night. Finish your sightseeing early on the 4th (Sat) to allow enough time to drive to Dennis.

Things to do in Plymouth

Museums · Outdoors · Historic Sites · Wildlife

Side Trips

Dennis

— 4 nights
Dennis is a town in Barnstable County, Massachusetts, United States, located near the center of Cape Cod. Edward Gorey House and Salt Pond Visitor Center will appeal to museum buffs. Discover out-of-the-way places like Skaket Beach and Corporation Beach. Take a break from Dennis with a short trip to Coast Guard Beach in Eastham, about 32 minutes away. Next up on the itinerary: kick back and relax at Mayflower Beach, stroll through Bass River Beach, get to know the fascinating history of Fort Hill Rural Historic District, and steep yourself in history at First Encounter Beach.

For traveler tips, where to stay, ratings, and tourist information, read our Dennis trip itinerary maker.

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 your sightseeing early on the 8th (Wed) so you can drive 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. Chatham Marconi Maritime Center and Atwood Museum are good opportunities to explore the local culture. You'll get in some beach time at Nauset Beach and Harding Beach. There's much more to do: look for all kinds of wild species at Monomoy National Wildlife Refuge, walk around Kate Gould Park, steep yourself in history at Chatham's Godfrey Windmill, and enjoy the sand and surf at Ridgevale Beach.

For photos, traveler tips, other places to visit, and tourist information, use the Chatham trip planning site.

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 your sightseeing early on the 12th (Sun) to allow enough time to drive 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.
Discover out-of-the-way places like Herring Cove Beach and Wellfleet Bay Wildlife Sanctuary. Visiting Cape Cod Provincelands Trail and Marconi Beach will get you outdoors. There's still lots to do: kick back and relax at Long Point, appreciate the history behind Pilgrim Monument & Provincetown Museum, get a sense of history and politics at Provincetown Town Hall, and stroll through Cape Cod National Seashore.

To find maps, reviews, traveler tips, and other tourist information, read our Provincetown holiday maker tool.

Drive from Chatham to Provincetown in an hour. Alternatively, you can take a bus. In July in Provincetown, expect temperatures between 30°C during the day and 20°C at night. Cap off your sightseeing on the 16th (Thu) early enough to travel to Nantucket.

Things to do in Provincetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Nantucket

— 6 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. You'll explore the less-touristy side of things at Cisco Brewers and Madaket Beach. Brant Point Lighthouse and Nantucket United Methodist Church will appeal to history buffs. And it doesn't end there: visit a coastal fixture at Sankaty Head Lighthouse, take in the architecture and atmosphere at St Paul's Episcopal Church, kick back and relax at Jetties Beach, and stroll through Siasconset Beach.

To see ratings, traveler tips, more things to do, and other tourist information, read Nantucket driving holiday planner.

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. Finish your sightseeing early on the 22nd (Wed) so you can travel 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.