28 days in Massachusetts Itinerary

28 days in Massachusetts Itinerary

Created using Inspirock Massachusetts trip itinerary planner

Make it your trip
Fly to General Edward Lawrence Logan International Airport, Drive to Fitchburg
1
Fitchburg
— 4 nights
Drive
2
Great Barrington
— 4 nights
Drive
3
Falmouth
— 4 nights
Drive
4
Provincetown
— 5 nights
Fly
5
Boston
— 10 nights
Fly

S M T W T F S
31
1
2
3
4
5
6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
1
2
3
4
5
6

Fitchburg

— 4 nights
Fitchburg is the third largest city in Worcester County, Massachusetts, United States. Kids will appreciate attractions like Great Wolf Lodge - Water Park and Mass Central Rail Trail. Get out of town with these interesting Fitchburg side-trips: Nashua River Rail Trail (in Pepperell), Animal Adventures Family Zoo & Rescue Center (in Bolton) and Northfield Mountain Cross Country Ski Area (in Northfield). On the 2nd (Tue), dedicate a day to the elevated beauty of Wachusett Mountain Ski Area. There's much more to do: take in the awesome beauty at Wachusett Mountain State Reservation, see the interesting displays at Museum of Russian Icons, explore the world behind art at Fitchburg Art Museum, and relax in the rural setting at Crystal Brook Farm.

To see reviews, other places to visit, photos, and tourist information, go to the Fitchburg journey builder.

Orlando to Fitchburg is an approximately 6.5-hour combination of flight and car. You can also drive. Plan for much colder temperatures traveling from Orlando in February, with highs in Fitchburg at 38°F and lows at 18°F. Finish up your sightseeing early on the 5th (Fri) so you can travel to Great Barrington.

Things to do in Fitchburg

Parks · Outdoors · Winter Sports · Nature

Side Trips

Great Barrington

— 4 nights
Great Barrington is a town in Berkshire County, Massachusetts, United States. Family-friendly places like Ski Butternut and Jiminy Peak Mountain Resort will thrill your kids. Change things up with these side-trips from Great Barrington: Otis Ridge (in Otis), The Clark Art Institute (in Williamstown) and Maple Corner Farm Cross Country Ski Area (in Granville). There's lots more to do: glide through natural beauty at Notchview, trek along Ashuwillticook Rail Trail, hit the slopes at Catamount Mountain Resort, and make a trip to W.E.B. DuBois Birthplace.

To find reviews, maps, and other tourist information, refer to the Great Barrington day trip app.

You can drive from Fitchburg to Great Barrington in 2.5 hours. February in Great Barrington sees daily highs of 34°F and lows of 15°F at night. Finish your sightseeing early on the 9th (Tue) so you can travel to Falmouth.

Things to do in Great Barrington

Outdoors · Winter Sports · Parks · Museums

Side Trips

Falmouth

— 4 nights
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Kids will enjoy Shining Sea Bikeway and Heritage Museums & Gardens. Venture out of the city with trips to Cape Cod Canal (in Buzzards Bay), Plymouth (Mayflower II & Plymouth Rock) and John F Kennedy Hyannis Museum (in Hyannis). The adventure continues: deepen your understanding at Cape Cod Children's Museum, see the interesting displays at Falmouth Museums on the Green, tee off at Farm Neck Golf Club, and take an in-depth tour of Sandwich Glass Museum.

For photos, ratings, and tourist information, use the Falmouth trip itinerary planning site.

Drive from Great Barrington to Falmouth in 3.5 hours. Expect somewhat warmer temperatures when traveling from Great Barrington in February; daily highs in Falmouth reach 40°F and lows reach 22°F. Wrap up your sightseeing on the 13th (Sat) to allow time to drive to Provincetown.

Things to do in Falmouth

Museums · Parks · Outdoors · Childrens Museums

Side Trips

Provincetown

— 5 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.
Bring the kids along to Race Point Beach and Herring Cove Beach. You'll find plenty of places to visit near Provincetown: Chatham (Chatham Lighthouse Beach & Chatham Railroad Museum) and Eastham (Coast Guard Beach & Captain Penniman House). There's still lots to do: appreciate the history behind Pilgrim Monument & Provincetown Museum, enjoy the sand and surf at Cape Cod National Seashore, make a trip to Commercial Street, and examine the collection at Provincetown Art Association and Museum.

For more things to do, other places to visit, reviews, and more tourist information, refer to the Provincetown planner.

Traveling by car from Falmouth to Provincetown takes 2 hours. Alternatively, you can take a bus. In February, plan for daily highs up to 38°F, and evening lows to 27°F. Finish up your sightseeing early on the 18th (Thu) so you can travel to Boston.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Boston

— 10 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.
Kids will appreciate attractions like Museum of Fine Arts and Museum of Science. You'll find plenty of places to visit near Boston: Salem (Salem Witch Museum, Peabody Essex Museum, &more). And it doesn't end there: observe the fascinating underwater world at New England Aquarium, explore the world behind art at Isabella Stewart Gardner Museum, browse the different shops at Faneuil Hall Marketplace, and explore the engaging exhibits at Boston Children's Museum.

For reviews, where to stay, other places to visit, and tourist information, go to the Boston online trip itinerary maker.

Getting from Provincetown to Boston by flight takes about 2 hours. Other options: ride a ferry; or drive. Expect a daytime high around 39°F in February, and nighttime lows around 24°F. Wrap up your sightseeing on the 28th (Sun) to allow time to travel back home.

Things to do in Boston

Museums · Parks · Shopping · Historic Sites

Side Trips

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.