30 days in Massachusetts Itinerary

30 days in Massachusetts Itinerary

Created using Inspirock Massachusetts holiday planner

Make it your trip
Fly to Logan International Airport, Drive to Sturbridge
1
Sturbridge
— 5 nights
Drive
2
Pittsfield
— 4 nights
Drive
3
Provincetown
— 5 nights
Drive
4
Falmouth
— 3 nights
Drive
5
Boston
— 11 nights
Fly

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Sturbridge

— 5 nights
Sturbridge is a town in Worcester County, Massachusetts, United States. Get out of town with these interesting Sturbridge side-trips: Union Station (in Worcester), Museum of Russian Icons (in Clinton) and The Gate Escape (in Leominster). There's much more to do: get engrossed in the history at Old Sturbridge Village, examine the collection at Basketball Hall of Fame, contemplate in the serene atmosphere at St. Anne's Shrine, and stroll around Forest Park.

To find where to stay, reviews, more things to do, and tourist information, refer to the Sturbridge online travel planner.

Perth, Australia to Sturbridge is an approximately 33-hour combination of flight and car. Traveling from Perth to Sturbridge, you'll gain 13 hours due to the time zone difference. Traveling from Perth in January, things will get colder in Sturbridge: highs are around 0°C and lows about -9°C. Finish up your sightseeing early on the 6th (Wed) so you can go by car to Pittsfield.

Things to do in Sturbridge

Museums · Historic Sites · Parks · Childrens Museums

Side Trips

Pittsfield

— 4 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Explore the numerous day-trip ideas around Pittsfield: Williamstown (The Clark Art Institute & Where'd You Get That!?, Inc.), Maple Corner Farm Cross Country Ski Area (in Granville) and Chester Railway Station (in Chester). Next up on the itinerary: head outdoors with Ramblewild, take in the spiritual surroundings of Congregational Church, explore the world behind art at Norman Rockwell Museum, and view the masterpieces at Ozzie's Glass Gallery.

For other places to visit, reviews, ratings, and more tourist information, read Pittsfield tour planner.

Traveling by car from Sturbridge to Pittsfield takes 1.5 hours. Expect a daytime high around 0°C in January, and nighttime lows around -11°C. Cap off your sightseeing on the 10th (Sun) early enough to travel to Provincetown.

Things to do in Pittsfield

Outdoors · Parks · Museums · Adventure

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.
Get out of town with these interesting Provincetown side-trips: Eastham (Nauset Light Beach, Salt Pond Visitor Center, &more), Orleans (Nauset Beach & Addison Art Gallery) and Chatham (Chatham Railroad Museum & Chatham Lighthouse). There's still lots to do: don't miss a visit to Commercial Street, kick back and relax at Long Point, tour the pleasant surroundings at Marconi Beach, and get a sense of history and politics at Provincetown Town Hall.

For maps, other places to visit, traveler tips, and tourist information, go to the Provincetown planning tool.

Getting from Pittsfield to Provincetown by car takes about 4.5 hours. Plan for somewhat warmer temperatures traveling from Pittsfield in January, with highs in Provincetown at 3°C and lows at -3°C. Finish up your sightseeing early on the 15th (Fri) so you can go by car to Falmouth.

Things to do in Provincetown

Parks · Outdoors · Beaches · Museums

Side Trips

Falmouth

— 3 nights
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Venture out of the city with trips to Plymouth Rock (in Plymouth), Heritage Museums & Gardens (in Sandwich) and Chatham (Chatham Lighthouse Beach, Monomoy National Wildlife Refuge, &more). There's still lots to do: explore the landscape on two wheels at Shining Sea Bikeway, enjoy the sea views from Nobska Point Lighthouse, get curious at Sandwich Glass Museum, and examine the collection at New Bedford Whaling Museum.

For other places to visit, more things to do, photos, and tourist information, use the Falmouth trip tool.

Traveling by car from Provincetown to Falmouth takes 2 hours. Alternatively, you can take a bus. Plan for slightly colder nights when traveling from Provincetown in January since evenings lows in Falmouth dip to -6°C. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Boston.

Things to do in Falmouth

Museums · Parks · Outdoors · Wildlife

Side Trips

Boston

— 11 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.
Venture out of the city with trips to Concord (Walden Pond State Reservation & Louisa May Alcott's Orchard House) and National Shrine of our Lady of La Salette (in Attleboro). There's much more to do: explore the world behind art at Museum of Fine Arts, take a stroll through North End, engage your brain at Museum of Science, and stroll around Boston Public Garden.

Discover how to plan a Boston trip in just a few steps with Inspirock's itinerary builder.

Getting from Falmouth to Boston by car takes about 1.5 hours. Other options: take a bus. In January, daily temperatures in Boston can reach 3°C, while at night they dip to -5°C. Finish your sightseeing early on the 29th (Fri) so you can fly back home.

Things to do in Boston

Museums · Historic Sites · Shopping · Parks

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.