15 days in Massachusetts Itinerary

15 days in Massachusetts Itinerary

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Route & dates

15 days in Massachusetts Itinerary

Start: Bakersfield
Fly + Drive:  13​h
1
Stockbridge
— 1 night
Drive + ferry:  4​h 30​min
2
Nantucket
— 3 nights
Drive:  2​h 45​min
3
Sandwich
— 4 nights
bus:  1​h
4
Boston
— 5 nights
Fly:  10​h 45​min
End: Bakersfield

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. On the 20th (Sun), contemplate the long history of Hancock Shaker Village, explore the world behind art at The Clark Art Institute, and then have some family-friendly fun at The Berkshire Carousel. Here are some ideas for day two: admire the masterpieces at Norman Rockwell Museum, then browse the exhibits of The Mount, Edith Wharton's Home, and then take in the spiritual surroundings of National Shrine of the Divine Mercy.

To see maps, other places to visit, and more tourist information, go to the Stockbridge tour planning site .

Bakersfield to Stockbridge is an approximately 13-hour combination of flight and car. You can also drive. You'll lose 3 hours traveling from Bakersfield to Stockbridge due to the time zone difference. Traveling from Bakersfield in October, you will find days in Stockbridge are much colder (60°F), and nights are a bit cooler (40°F). Cap off your sightseeing on the 21st (Mon) early enough to travel to Nantucket.

Things to do in Stockbridge

Museums Historic Sites Fun & Games

Side Trips

Pittsfield, The Clark Art Institute, The Mount, Edith Wharton's Home
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
The Clark Art Institute ©
The Clark Art Institute
The Mount, Edith Wharton's Home ©
The Mount, Edith Wharton's Home

3
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Museum-lovers will get to explore Whaling Museum and Egan Maritime's Nantucket Shipwreck & Lifesaving Museum. Popular historic sites such as Great Point Light and Sankaty Head Lighthouse are in your itinerary. And it doesn't end there: appreciate the extensive heritage of Milestone Bog, make a trip to Brant Point Lighthouse, contemplate the long history of Oldest House (Jethro Coffin House) and Kitchen Garden, and see the interesting displays at Nantucket Lightship Basket Museum.

To see other places to visit, photos, and more tourist information, you can read our Nantucket day trip planning website .

Traveling by combination of car and ferry from Stockbridge to Nantucket takes 4.5 hours. Alternatively, you can do a combination of bus and flight; or do a combination of bus and ferry. Traveling from Stockbridge in October, plan for a bit warmer nights in Nantucket, with lows around 51°F. Finish up your sightseeing early on the 24th (Thu) so you can go by car to Sandwich.

Things to do in Nantucket

Historic Sites Museums Parks
Highlights from your plan
Great Point Light ©
Great Point Light
Whaling Museum ©
Whaling Museum
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse

4
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Deepen your sense of the past at sights like Edward Gorey House and Trinity Park Tabernacle. Appreciate the collections at Heritage Museums & Gardens and Plimoth Plantation. Explore the numerous day-trip ideas around Sandwich: Chatham Marconi Maritime Center (in North Chatham), Provincetown (Pilgrim Monument & Provincetown Museum & MacMillan Wharf) and Lizzie Borden House (in Fall River). Next up on the itinerary: engage your brain at Sandwich Glass Museum, enjoy the sea views from Edgartown Lighthouse, get to know the fascinating history of Cornelia Carey Sanctuary (The Knob), and steep yourself in history at Hoxie House.

To see photos, where to stay, and more tourist information, read our Sandwich trip builder site .

You can drive from Nantucket to Sandwich in 3 hours. Traveling from Nantucket in October, Sandwich is a bit cooler at night with lows of 46°F. Wrap up your sightseeing on the 28th (Mon) early enough to take a bus to Boston.

Things to do in Sandwich

Museums Historic Sites Parks

Side Trips

Plymouth, Provincetown, Edgartown, Trinity Park Tabernacle, Cornelia Carey Sanctuary (The Knob)
Highlights from your plan
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation

5
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.
Freedom Trail and Mount Auburn Cemetery will appeal to history buffs. Let the collections at Museum of Fine Arts and John F. Kennedy Presidential Museum & Library capture your imagination. Explore Boston's surroundings by going to The Needham Free Public Library (in Needham), Salem (Salem Witch Museum & The House of the Seven Gables) and The Fairbanks House (in Dedham). There's lots more to do: take an in-depth tour of Boston Tea Party Ships & Museum, contemplate in the serene atmosphere at Trinity Church, steep yourself in history at Louisa May Alcott's Orchard House, and explore the galleries of The Paul Revere House.

To find where to stay, other places to visit, traveler tips, and other tourist information, read Boston route planning site .

You can take a bus from Sandwich to Boston in an hour. Another option is to drive. In October in Boston, expect temperatures between 64°F during the day and 50°F at night. Finish your sightseeing early on the 2nd (Sat) to allow enough time to travel back home.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Concord, Salem, The Fairbanks House, Mount Auburn Cemetery, The Needham Free Public Library
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

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