27 days in Massachusetts Itinerary

27 days in Massachusetts Itinerary

Created using Inspirock Massachusetts travel route planner

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Route & dates

27 days in Massachusetts Itinerary

Start: Boston
1
Boston
— 4 nights
Train:  45 min
2
Concord
— 2 nights
Drive:  30 min
3
Bolton
— 1 night
Drive:  15 min
4
Clinton
— 1 night
Drive:  15 min
5
Boylston
— 1 night
Drive:  30 min
6
Worcester
— 2 nights
Drive + Ferry:  3 h
7
Nantucket
— 2 nights
Drive:  2 h 30 min
8
Oak Bluffs, Martha's Vineyard
— 1 night
Drive:  1 h 15 min
9
Falmouth
— 2 nights
Bus:  45 min
10
Hyannis
— 4 nights
Drive:  15 min
11
Barnstable
— 2 nights
Drive:  30 min
12
West Harwich
— 1 night
Drive:  1 h
13
Provincetown
— 3 nights
Ferry:  1 h 30 min
End: Boston

4
nights
Boston

Boston ©
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 Marginal Way Walkway (in Ogunquit), The House of the Seven Gables (in Salem) and Dolphin & Whale Watching (in Gloucester). There's much more to do: explore the world behind art at Museum of Fine Arts, get to know the fascinating history of Freedom Trail, browse the collection at Boston Public Library, and stroll around Boston Common.

To find reviews, traveler tips, maps, and more tourist information, you can read our Boston sightseeing planner.

Use the Route module to find travel options from your starting location to Boston. In November, plan for daily highs up to 52°F, and evening lows to 37°F. Wrap up your sightseeing on the 14th (Thu) early enough to take a train to Concord.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Salem, Marginal Way Walkway, Dolphin & Whale Watching
Find places to stay Nov 10 — 14:
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Marginal Way Walkway ©
Marginal Way Walkway

2
nights
Concord

Concord ©
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 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 see where to stay, photos, and tourist information, read our Concord road trip tool.

Take a train from Boston to Concord in an hour. Alternatively, you can drive; 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.

Things to do in Concord

Historic Sites Parks Nature
Find places to stay Nov 14 — 16:
Highlights from your plan
Walden Pond State Reservation ©
Walden Pond State Reservation
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
North Bridge ©
North Bridge

1
night
Bolton

Bolton ©
Bolton is a town in Worcester County, Massachusetts, United States. Your day-by-day itinerary now includes Nashoba Valley Winery. Kick off your visit on the 17th (Sun): do a tasting at Nashoba Valley Winery, then meet the residents at Animal Adventures, and then relax in the rural setting at Bolton Orchards.

For more things to do, other places to visit, ratings, and other tourist information, read Bolton tour itinerary website.

Bolton is just a short distance from Concord. In November in Bolton, expect temperatures between 51°F during the day and 32°F at night. Cap off your sightseeing on the 17th (Sun) early enough to travel to Clinton.

Things to do in Bolton

Parks Wineries Zoos & Aquariums
Find places to stay Nov 16 — 17:
Highlights from your plan
Nashoba Valley Winery ©
Nashoba Valley Winery
Bolton Orchards ©
Bolton Orchards

1
night
Clinton

Clinton ©
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.

To find traveler tips, maps, reviews, 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 travel to Boylston.

Things to do in Clinton

Fun & Games Parks

Side Trip

Sterling
Find places to stay Nov 17 — 18:
Highlights from your plan
Davis Farmland ©
Davis Farmland
Clearview Farm ©
Clearview Farm
Central Park ©
Central Park

1
night
Boylston

Boylston ©
Boylston is a town in Worcester County, Massachusetts, United States. Your day-by-day itinerary now includes Tower Hill Botanic Garden. Start off your visit on the 19th (Tue): take in nature's colorful creations at Tower Hill Botanic Garden, 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 see traveler tips, maps, more things to do, 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.

Things to do in Boylston

Parks Historic Sites

Side Trips

Northborough, Indian Head Farm
Find places to stay Nov 18 — 19:
Highlights from your plan
Tower Hill Botanic Garden ©
Tower Hill Botanic Garden
Indian Head Farm ©
Indian Head Farm
Tougas Family Farm ©
Tougas Family Farm

2
nights
Worcester

Worcester ©
Worcester is a city and the county seat of Worcester County, Massachusetts, United States. The Hanover Theatre and Conservatory for the Performing Arts has been added to your itinerary. Kick off your visit on the 16th (Sat): see a show at The Hanover Theatre and Conservatory for the Performing Arts, admire the striking features of Union Station, then test your problem-solving skills at popular escape rooms, then explore the world behind art at Worcester Art Museum, and finally enjoy some diversion at Central Rock Gym. Keep things going the next day: take an in-depth tour of Old Sturbridge Village and then browse the eclectic array of goods at Crompton Collective.

For reviews, other places to visit, traveler tips, and other tourist information, read our Worcester journey maker website .

Worcester is just a short distance from Boylston. In November, plan for daily highs up to 48°F, and evening lows to 32°F. Cap off your sightseeing on the 17th (Sun) early enough to travel to Nantucket.

Things to do in Worcester

Museums Fun & Games Nightlife

Side Trip

Old Sturbridge Village
Find places to stay Nov 19 — 21:
Highlights from your plan
Worcester Art Museum ©
Worcester Art Museum
Old Sturbridge Village ©
Old Sturbridge Village

2
nights
Nantucket

Nantucket ©
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 Egan Maritime's Nantucket Shipwreck & Lifesaving Museum.

To find photos, where to stay, reviews, and more tourist information, refer to the Nantucket online trip planner.

Traveling by combination of car and ferry from Worcester to Nantucket takes 3 hours. Alternatively, you can do a combination of bus and flight; 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 go by car to Oak Bluffs.

Things to do in Nantucket

Parks Outdoors Beaches
Find places to stay Nov 21 — 23:
Highlights from your plan
Madaket Beach ©
Madaket Beach
Whaling Museum ©
Whaling Museum
Great Point Light ©
Great Point Light

1
night
Oak Bluffs, Martha's Vineyard

Oak Bluffs ©
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).

To find ratings, other places to visit, photos, and tourist information, read Oak Bluffs trip planner.

Getting from Nantucket to Oak Bluffs by car takes about 2.5 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 go by car to Falmouth.

Things to do in Oak Bluffs

Historic Sites Neighborhoods

Side Trip

Edgartown Lighthouse
Find places to stay Nov 23 — 24:
Highlights from your plan
Trinity Park Tabernacle ©
Trinity Park Tabernacle
Edgartown Lighthouse ©
Edgartown Lighthouse
Flying Horses Carousel ©
Flying Horses Carousel

2
nights
Falmouth

Falmouth ©
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 see photos, traveler tips, more things to do, and other tourist information, you can read our Falmouth trip itinerary planner.

Traveling by car from Oak Bluffs to Falmouth takes 1.5 hours. 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 take a bus to Hyannis.

Things to do in Falmouth

Parks Museums Historic Sites

Side Trip

Lizzie Borden House
Find places to stay Nov 24 — 26:
Highlights from your plan
Woods Hole Science Aquarium ©
Woods Hole Science Aquarium
Lizzie Borden House ©
Lizzie Borden House
Falmouth Museums on the Green ©
Falmouth Museums on the Green

4
nights
Hyannis

Hyannis ©
"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Hyannis is known for museums, breweries & distilleries, and beaches. Your plan includes some of its best attractions: see the interesting displays at John F Kennedy Hyannis Museum, pause for some photo ops at John F. Kennedy Memorial, tour the pleasant surroundings at Craigville Beach, and stop by Main Street Hyannis.

To see traveler tips, other places to visit, maps, and other tourist information, go to the Hyannis holiday planner.

Take a bus from Falmouth to Hyannis in an hour. Alternatively, you can drive. In November, daytime highs in Hyannis are 53°F, while nighttime lows are 37°F. Finish your sightseeing early on the 30th (Sat) to allow enough time to drive to Barnstable.

Things to do in Hyannis

Parks Outdoors Beaches

Side Trips

West Yarmouth, Chapman Art Gallery, Pirate's Cove, Osterville Village Library, Cape Cod Maritime Museum
Find places to stay Nov 26 — 30:
Highlights from your plan
Craigville Beach ©
Craigville Beach
John F Kennedy Hyannis Museum ©
John F Kennedy Hyannis Museum
St. Francis Xavier Church ©
St. Francis Xavier Church

2
nights
Barnstable

Barnstable ©
Barnstable is a city, referred to as the Town of Barnstable, in the U.S. You've now added Hyannis Whale Watcher Cruises to your itinerary. Kick off your visit on the 1st (Sun): take a memorable tour with Hyannis Whale Watcher Cruises, steep yourself in history at Edward Gorey House, then contemplate the long history of Captain Bangs Hallet House Museum, and finally get a taste of the local shopping with Samuell Day Gallery. Get ready for a full day of sightseeing on the next day: identify plant and animal life at Long Pasture Wildlife Sanctuary, then enjoy the sand and surf at Gray's Beach, and then contemplate the long history of Sturgis Library.

To see traveler tips, ratings, reviews, and tourist information, refer to the Barnstable journey maker tool .

Barnstable is just a stone's throw from Hyannis. In November, plan for daily highs up to 53°F, and evening lows to 37°F. Finish up your sightseeing early on the 2nd (Mon) so you can travel to West Harwich.

Things to do in Barnstable

Outdoors Wildlife Historic Sites

Side Trip

Yarmouth Port
Find places to stay Nov 30 — Dec 2:
Highlights from your plan
Hyannis Whale Watcher Cruises ©
Hyannis Whale Watcher Cruises
Edward Gorey House ©
Edward Gorey House
Captain Bangs Hallet House Museum ©
Captain Bangs Hallet House Museum

1
night
West Harwich

West Harwich ©
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.

To see where to stay, ratings, 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 travel to Provincetown.

Things to do in West Harwich

Parks Outdoors Beaches

Side Trips

Chatham Lighthouse Beach, Captain Penniman House, Nauset Beach, First Crush Winery Cape Cod
Find places to stay Dec 2 — 3:
Highlights from your plan
Nauset Beach ©
Nauset Beach
Chatham Lighthouse Beach ©
Chatham Lighthouse Beach
Captain Penniman House ©
Captain Penniman House

3
nights
Provincetown

Provincetown ©
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 wildlife, beaches, and nightlife. Your plan includes some of its best attractions: pause for some photo ops at Pilgrim Monument & Provincetown Museum, take a tour by water with Boat Tours & Water Sports, kick back and relax at Race Point Beach, and stroll through Province Lands Bike Trail.

To see photos, ratings, more things to do, 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 ride a ferry back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Uncle Tim's Bridge, Cape Cod National Seashore
Find places to stay Dec 3 — 6:
Highlights from your plan
Race Point Beach ©
Race Point Beach
Cape Cod National Seashore ©
Cape Cod National Seashore

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