27 days in Massachusetts Itinerary

27 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel route planner
Make it your trip
1
Boston
— 4 nights
Drive
2
Concord
— 2 nights
Drive
3
Bolton
— 1 night
Drive
4
Clinton
— 1 night
Drive
5
Boylston
— 1 night
Drive
6
Worcester
— 2 nights
Fly
7
Nantucket
— 2 nights
Ferry
8
Oak Bluffs, Martha's Vineyard
— 1 night
Ferry
9
Falmouth
— 2 nights
Drive
10
Hyannis
— 4 nights
Drive
11
Barnstable
— 2 nights
Drive
12
West Harwich
— 1 night
Drive
13
Provincetown
— 3 nights
Fly

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Boston — 4 nights

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.
Explore Boston's surroundings by going to Salem (The House of the Seven Gables & Fished Impressions), Dolphin & Whale Watching (in Gloucester) and Marginal Way Walkway (in Ogunquit). There's lots more to do: explore the world behind art at Museum of Fine Arts, take in nature's colorful creations at Boston Public Garden, take an in-depth tour of Boston Tea Party Ships & Museum, and get lost in a book at Boston Public Library.

To see photos, traveler tips, reviews, and other tourist information, refer to the Boston online itinerary planner.

Use the Route module to find travel options from your starting location to Boston. November in Boston sees daily highs of 52°F and lows of 37°F at night. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to Concord.
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Museums · Historic Sites · Tours · Parks
Side Trips

Concord — 2 nights

Concord is a town in Middlesex County, Massachusetts, in the United States. Walden Pond State Reservation has been added to your itinerary. Kick off your visit on the 15th (Fri): snap pictures at The Old North Bridge, make a trip to The Old Manse, then contemplate the waterfront views at Walden Pond State Reservation, and finally explore the different monuments and memorials at Sleepy Hollow Cemetery. On your second day here, take in the history at Minute Man National Historical Park, steep yourself in history at Louisa May Alcott's Orchard House, then get engrossed in the history at Concord Museum, and finally don't miss a visit to Monument Square.

To find ratings, maps, reviews, and tourist information, read our Concord road trip tool.

Drive from Boston to Concord in an hour. Alternatively, you can take a train; or take a bus. Traveling from Boston in November, expect slightly colder with lows of 31°F in Concord. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Bolton.
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Historic Sites · Parks · Nature · Museums

Bolton — 1 night

Bolton is a town in Worcester County, Massachusetts, United States. Your day by day itinerary now includes Nashoba Valley Winery. On the 17th (Sun), do a tasting at Nashoba Valley Winery and then experience rural life at Bolton Orchards.

To see more things to do, maps, photos, and other tourist information, read Bolton trip planner.

Bolton is very close to Concord. In November, plan for daily highs up to 51°F, and evening lows to 32°F. Wrap up your sightseeing on the 17th (Sun) early enough to drive to Clinton.
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Wineries

Clinton — 1 night

Clinton is a town in Worcester County, Massachusetts, United States. Start off your visit on the 18th (Mon): walk around Central Park, get your game on at Davis Farmland, then relax in the rural setting at Crystal Brook Farm, and finally experience rural life at Clearview Farm.

For photos, reviews, where to stay, and other tourist information, read our Clinton trip planner.

Clinton is very close to Bolton. In November, daytime highs in Clinton are 51°F, while nighttime lows are 32°F. Finish your sightseeing early on the 18th (Mon) so you can drive to Boylston.
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Fun & Games · Parks
Side Trip

Boylston — 1 night

Boylston is a town in Worcester County, Massachusetts, United States. Your day by day itinerary now includes New England Botanic Garden at Tower Hill. Start off your visit on the 19th (Tue): take in nature's colorful creations at New England Botanic Garden at Tower Hill, relax in the rural setting at Tougas Family Farm, then steep yourself in history at Mary Goodnow's Grave, and finally experience rural life at Indian Head Farm.

To find where to stay, ratings, maps, and more tourist information, go to the Boylston trip maker.

Boylston is just a short distance from Clinton. In November in Boylston, expect temperatures between 51°F during the day and 32°F at night. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Worcester.
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Parks · Historic Sites
Side Trips

Worcester — 2 nights

Worcester is a city and the county seat of Worcester County, Massachusetts, United States. You've now added The Hanover Theatre and Conservatory for the Performing Arts to your itinerary. Start off your visit on the 20th (Wed): see a show at The Hanover Theatre and Conservatory for the Performing Arts, don't miss a visit to Union Station, test your team's savvy at popular escape rooms, then admire the masterpieces at Worcester Art Museum, and finally have fun at Central Rock Gym. Get ready for a full day of sightseeing on the 21st (Thu): take an in-depth tour of Old Sturbridge Village and then pick up a one of a kind souvenir at Crompton Collective.

To see photos, reviews, and other tourist information, use the Worcester trip itinerary tool.

Worcester is just a stone's throw from Boylston. In November, plan for daily highs up to 48°F, and evening lows to 32°F. Wrap up your sightseeing on the 21st (Thu) to allow time to fly to Nantucket.
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Museums · Fun & Games · Nightlife · Shopping
Side Trip

Nantucket — 2 nights

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Start off your visit on the 22nd (Fri): see the interesting displays at Whaling Museum, enjoy the sea views from Sankaty Head Lighthouse, and then visit a coastal fixture at Great Point Light. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Jetties Beach, then enjoy the sand and surf at Madaket Beach, and then take an in-depth tour of Nantucket Shipwreck & Lifesaving Museum.

To see where to stay, reviews, more things to do, and more tourist information, refer to the Nantucket online trip planner.

Traveling by flight from Worcester to Nantucket takes 2.5 hours. Alternatively, you can do a combination of car and ferry; or do a combination of bus and ferry. Traveling from Worcester in November, expect a bit warmer with lows of 41°F in Nantucket. Finish up your sightseeing early on the 23rd (Sat) so you can catch the ferry to Oak Bluffs.
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Beaches · Outdoors · Parks · Museums

Oak Bluffs, Martha's Vineyard — 1 night

Oak Bluffs is a town located on the island of Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 24th (Sun): relax in the rural setting at Island Alpaca Company of Martha's Vineyard, enjoy the sea views from Edgartown Lighthouse, admire the striking features of Trinity Park Tabernacle, then make a trip to Flying Horses Carousel, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

For ratings, maps, photos, and tourist information, read Oak Bluffs trip planner.

Getting from Nantucket to Oak Bluffs by ferry takes about 2 hours. In November, daily temperatures in Oak Bluffs can reach 53°F, while at night they dip to 37°F. Cap off your sightseeing on the 24th (Sun) early enough to catch the ferry to Falmouth.
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Historic Sites · Neighborhoods
Side Trip

Falmouth — 2 nights

Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. You've now added Cape Cod Winery to your itinerary. Kick off your visit on the 25th (Mon): visit a coastal fixture at Nobska Point Lighthouse, then explore the landscape on two wheels at Shining Sea Bikeway, then learn about winemaking at Cape Cod Winery, and finally admire the natural beauty at Spohr Gardens. Get ready for a full day of sightseeing on the 26th (Tue): contemplate the long history of Lizzie Borden House, then get up close and personal with brilliant marine life at Woods Hole Science Aquarium, and then see the interesting displays at Falmouth Museums on the Green.

To find ratings, other places to visit, more things to do, and other tourist information, you can read our Falmouth trip itinerary planner.

Traveling by ferry from Oak Bluffs to Falmouth takes an hour. Alternatively, you can do a combination of ferry and taxi. November in Falmouth sees daily highs of 53°F and lows of 35°F at night. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Hyannis.
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Parks · Museums · Historic Sites · Trails
Side Trip

Hyannis — 4 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Hyannis is known for museums, sightseeing, and breweries & distilleries. Your trip includes some of its best attractions: examine the collection at John F Kennedy Hyannis Museum, kick back and relax at Kalmus Beach, pick up a one of a kind souvenir at Antiques Center of Yarmouth, and contemplate in the serene atmosphere at St. Francis Xavier Church.

Plan my day in Hyannis using traveler tips and tourist information provided by Inspirock.

Drive from Falmouth to Hyannis in an hour. Alternatively, you can take a bus. In November, plan for daily highs up to 53°F, and evening lows to 37°F. Finish your sightseeing early on the 30th (Sat) so you can drive to Barnstable.
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Beaches · Outdoors · Parks · Shopping
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. You've now added Hyannis Whale Watcher Cruises to your itinerary. Start off your visit on the 1st (Sun): get up close to creatures of the deep with Hyannis Whale Watcher Cruises, browse the exhibits of Edward Gorey House, then contemplate the long history of Captain Bangs Hallet House Museum, and finally view the masterpieces at Samuell Day Gallery. Keep things going the next day: identify plant and animal life at Long Pasture Wildlife Sanctuary, kick back and relax at Gray's Beach, and then get your bearings at Sturgis Library Barnstable.

To find where to stay, traveler tips, photos, and tourist information, refer to the Barnstable trip itinerary planner.

Barnstable is very close to Hyannis. November in Barnstable sees daily highs of 53°F and lows of 37°F at night. Cap off your sightseeing on the 2nd (Mon) early enough to go by car to West Harwich.
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Outdoors · Wildlife · Historic Sites · Tours
Side Trip

West Harwich — 1 night

West Harwich is a village in the town of Harwich, Massachusetts, on Cape Cod, United States. First Crush Winery Cape Cod has been added to your itinerary. On the 3rd (Tue), steep yourself in history at Captain Penniman House, stroll through Nauset Beach, then kick back and relax at Chatham Lighthouse Beach, and finally learn about winemaking at First Crush Winery Cape Cod.

For reviews, where to stay, more things to do, and tourist information, use the West Harwich trip builder website.

West Harwich is just a short distance from Barnstable. In December, daytime highs in West Harwich are 45°F, while nighttime lows are 33°F. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to Provincetown.
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Beaches · Outdoors · Parks · Wineries
Side Trips

Provincetown — 3 nights

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.
Provincetown is known for sightseeing, wildlife, and beaches. Your trip includes some of its best attractions: kick back and relax at Herring Cove Beach, have fun and explore at Sea Space Marine Discovery Center, pause for some photo ops at Pilgrim Monument & Provincetown Museum, and shop like a local with Cortile Gallery.

To find maps, reviews, photos, and other tourist information, read our Provincetown travel route builder website.

Traveling by car from West Harwich to Provincetown takes an hour. In December, daily temperatures in Provincetown can reach 44°F, while at night they dip to 34°F. Finish your sightseeing early on the 6th (Fri) so you can fly back home.
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Outdoors · Parks · Beaches · Nature
Side Trips

Massachusetts travel guide

4.3
History Museums · Art Museums · Nightlife
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.
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