10 TOP Things to Do in Massachusetts October 2026

A street with autumn-colored trees, a building with a sign for 'EDYTHE & CO.', and a parked car.

A large, illuminated ship docked at a pier with fireworks in the background.

A wooden beach gate leading to a sandy beach with the ocean in the background.

A modern building with a prominent ICA sign, glass facade, and a waterfront location.

A brightly lit Paramount theater with illuminated marquee and signage.

Activities

Boston Old Town Trolley Hop-on Hop-Off City Tour

NZ$86

per adult

90% of travellers recommend

Go City: Boston All-Inclusive Pass with 45+ Attractions

NZ$124

per adult

80% of travellers recommend

Boston Harbor Cruise boat with the skyscrapers of the city in the background in Boston

City Cruises Boston: Historic Sightseeing Cruise

NZ$64

per adult

92% of travellers recommend

Boston CityPASS: Admission to Top 4 Boston Attractions

Boston CityPASS®: Admission to Top 4 Attractions

NZ$147

per adult

92% of travellers recommend

Go City: Boston Explorer Pass - Choose 2 to 5 Attractions

NZ$90

per adult

94% of travellers recommend

History and Hauntings of Salem Guided Walking Tour

NZ$63

per adult

98% of travellers recommend

Boston's Freedom Trail: A Revolutionary Walking Tour

NZ$54

per adult

98% of travellers recommend

Boston: Sunset Tall Ship Harbor Cruise

NZ$131

per adult

100% of travellers recommend

Boston: Freedom Trail History Small Group Walking Tour

NZ$94

per adult

100% of travellers recommend

See all activities in Massachusetts

Explore activities
Explore thousands of experiences from activities and attractions to day tours and transfer.
Book with ease
Skip the line- book tickets online in minutes to top attractions with free cancellation on many activities.
Treat yourself
Members save % or more when you book activities.

Top places to visit

1. Fenway Park

Fenway Park exudes sporting history and heritage. The home of the legendary Boston Red Sox is one of the oldest ballparks in America. If your visit coincides with a home fixture, treat yourself to a ticket and experience the heady atmosphere and excitement of this uniquely American passion.

Learn more

A cityscape with a prominent stadium, a busy intersection, and a skyline with high-rise buildings.

2. Harvard University

Harvard University, founded in 1636, is the oldest higher education institution in the USA and probably the best-known and most prestigious of the elite “Ivy League” universities. Its leafy campus occupies a 154-hectare site on the outskirts of Boston, which makes for a fascinating half-day excursion away from the bustle of “downtown”.

Learn more

A classical building with columns and a blue door, surrounded by trees and people walking.

3. Boston Common

Boston Common has a long, fascinating and often bloody history. This former cow pasture served as a British encampment during the American War of Independence, became a recruitment point during the Civil War, and was the site of public hangings until 1817. Since then it has been the rallying point for anti-slavery meetings and anti-war protests. Today it’s a favourite place for Bostonians to chill out and indulge in a little gentle exercise, while visitors flock here to start walking the Freedom Trail.

Learn more

A public park with a large fountain, surrounded by trees and modern buildings.

4. Copley Square

Copley Square is one of the jewels of the upmarket Back Bay area of downtown Boston. Locals come here to take a break from work, meet friends by the elegant fountain or shop at the bi-weekly farmers’ market, while visitors are drawn by its architecturally important buildings and harmonious ambience.

Learn more

A historic church with a pointed roof and a large tower, surrounded by modern buildings and a well-maintained park with flowers and trees.

5. Plymouth Harbor

Breathe in the salty sea air and step onto the creaky docks in Plymouth Harbor. A number of America’s most important historical sites surround you. In this picturesque harbor, you are just a short walk from the sites where America’s modern settlement first started.

Learn more

A harbor with multiple sailboats and a prominent ship named 'PILGRIM BELLE'.

What to do in Massachusetts

Stay near popular Massachusetts attractions

Fenway Park

9.2/10 (11,009 reviews)

The iconic home of the Boston Red Sox is on the must-see list of every red-blooded baseball fan.

See properties

Our guide on where to stay in Massachusetts

Find the best Massachusetts areas for the activities you enjoy most.

Quincy Market with an American flag, historic buildings, and a clock tower in the background.

Downtown Boston

Known for its must-see aquarium and captivating waterfront views, there's plenty to explore in Downtown Boston. Check out top attractions like Boston Massacre Site and Old State House, and jump on the metro at State St. Station or Downtown Crossing Station to see more of the city.

See properties

A historic church with a large central tower and multiple spires, surrounded by modern buildings and a public square with people and greenery.

Back Bay

Gourmet restaurants interesting history and top sights from Copley Square to Newbury Street – discover Back Bay, a destination also famous for its shopping.

See properties

A city skyline at dusk with illuminated buildings reflecting on the water, a prominent bridge, and a large chain barrier along the waterfront.

Seaport District

Travellers to Seaport District praise its captivating waterfront views. If you've got some more time to explore, be sure to stop by Liberty Wharf and Leader Bank Pavilion.

See properties

A large brick building with a golden dome, a flagpole with the American flag, and a statue in front.

Beacon Hill

Historical sites, shopping and restaurants highlight some notable features of Beacon Hill. Make a stop by Charles Street or Hatch Shell while you're visiting, and jump aboard the metro at Charles-MGH Station or Park St. Station to get around town.

See properties

A statue of a man on horseback in a park with trees, a clock tower, and brick buildings in the background.

North End

The ample dining options and captivating waterfront views are just a few popular features of the neighbourhood. Make a stop by Old North Church or Paul Revere House while you're visiting, and jump aboard the metro at Aquarium to get around town.

Looking for fun things to do nearby? Check things to do near me to find and book the best things to do, fun activities, and top attractions wherever you happen to be.