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A Boston bucket list starts with walking the 2.5-mile Freedom Trail, seeing a game or a tour at Fenway Park, eating chowder at Union Oyster House, open since 1826, and taking a ferry to the Harbor Islands. The 25 experiences below are the ones that are distinctly Boston, each checked against its official source on October 1, 2026, with the season or day that matters.
Boston Harbor Islands Ferry tickets
This page promised 100 things in its original version but covered three. Rather than pad it, we kept the list to experiences worth crossing off once. For a broader list of ideas, see our 100 things to do in Boston.
Revolutionary history
- Follow the Freedom Trail. A red line in the sidewalk links 16 historic sites from Boston Common to the Bunker Hill Monument in Charlestown. Following it is free; some sites charge admission.
- Climb to the bell chamber at Old North Church. Old North Church, opened in 1723, is where two lanterns were hung on April 18, 1775. The steeple is closed, but a 25-minute guided tour reaches the bell chamber for $15 with general admission.
- Step inside the Paul Revere House. Built about 1680, the Paul Revere House is downtown Boston's oldest building, and adult admission is $6.
- Board USS Constitution. The frigate launched in 1797 is still an active-duty Navy ship at the Charlestown Navy Yard. Boarding is free with photo ID for adults, and the USS Constitution Museum across the pier tells its story.
- Throw tea at the Boston Tea Party Ships. The Boston Tea Party Ships & Museum runs one-hour costumed tours on Fort Point Channel, close to where the 1773 protest took place.Boston Tea Party Ships & Museum tickets
- Tour the State House. Tours of the gold-domed Massachusetts State House are free on weekdays from 10 a.m. to 3:30 p.m.; the building is closed on weekends.
Sports and big days
- See the Green Monster. Fenway Park has been home to the Red Sox since April 20, 1912. Without a game ticket, the 60-minute tour runs every day of the year for $30.
- Have a beer inside Fenway. Bleacher Bar, under the center-field bleachers, looks straight onto the outfield through a garage-door window, and no game ticket is needed.
- Cheer at the Boston Marathon finish. The marathon finishes on Boylston Street in Back Bay on Patriots' Day; the 2027 race is on Monday, April 19.
- Spend July 4 on the Esplanade. The Boston Pops Fireworks Spectacular at the Hatch Shell is free and open to the public.
- Watch the Head of the Charles. The rowing regatta fills the Charles River between Boston and Cambridge on October 16 to 18, 2026, and watching from the riverbanks is free.
Museums and views
- Give a day to the MFA. The Museum of Fine Arts holds nearly 500,000 works, from ancient Egypt to contemporary art; it stays open until 10 p.m. on Thursdays and Fridays.
- See the Gardner, room by room. The Isabella Stewart Gardner Museum still hangs as its founder arranged it, empty frames from the 1990 theft included. Thursday evenings from 5 to 9 p.m. are free, and anyone named Isabella gets in free for life.
- Read in Bates Hall. The Boston Public Library's Central Library in Copley Square, the first large free municipal library in the country, is free to enter; its inner courtyard is a quiet place to sit.
- Watch sunset from the Prudential. View Boston fills the top three floors of the Prudential Tower, with an open-air terrace, from $32.
- Visit the JFK Library. The John F. Kennedy Presidential Library and Museum at Columbia Point faces the harbor; visitors 17 and under enter free.
Food and drink
- Eat chowder at the oldest restaurant. Union Oyster House calls itself the oldest restaurant in continuous service in the United States, and its oyster bar still stands where it was first installed. Our guide to Boston's oldest restaurants covers its rivals.
- Wait for a lobster roll at Neptune Oyster. Neptune Oyster on Salem Street takes no reservations, so go mid-afternoon to shorten the wait.
- Order a pie at the original Regina. Regina Pizzeria has made brick-oven pizza on Thacher Street in the North End since 1926.
- Raise a pint in an old tavern. The Bell in Hand near Faneuil Hall dates its first pour to 1795, and Charlestown's Warren Tavern was built in 1780.
Parks and the water
- Ride a Swan Boat. The pedal-powered boats in the Public Garden run daily from mid-April to early September for $4.75; the 2026 season has ended, and they return in April 2027. The Make Way for Ducklings statues are there year-round.
- Take the ferry to the Harbor Islands. Ferries to Georges and Spectacle islands in Boston Harbor Islands National and State Park leave Long Wharf North from mid-May to mid-October; October 12 is the last day of the 2026 season.
- Walk a stretch of the Harborwalk. The Boston Harborwalk runs about 43 miles along the shoreline; the stretch from Long Wharf to the Seaport makes a good first walk.
- Circle Castle Island. The path around Fort Independence on Pleasure Bay in South Boston is free, and the fort opens for free tours on summer weekends.
- Climb Peters Hill. The Arnold Arboretum in Jamaica Plain is free from sunrise to sunset, and the top of Peters Hill looks back over the trees to the skyline.
What you can still tick off this fall
In October, the Harbor Islands ferries run until October 12, the Head of the Charles is October 16 to 18, Fenway tours run daily, and the museums keep their usual hours. The Swan Boats are done until April. See our things to do in Boston in October for the rest of the month.
Frequently asked questions
Q. What should be on a Boston bucket list?
Walk the Freedom Trail, see Fenway Park, eat chowder at Union Oyster House, take a ferry to the Harbor Islands in summer, ride a Swan Boat in the Public Garden, and spend a day at the Museum of Fine Arts or the Gardner Museum.
Q. What is the oldest restaurant in Boston?
Union Oyster House at 41 Union Street, which has served food since 1826 and calls itself the oldest restaurant in continuous service in the United States.
Q. How many works are in the Museum of Fine Arts, Boston?
Nearly 500,000, according to the museum, ranging from ancient Egypt and Nubia to contemporary art.
Q. What Boston bucket list items are free?
The Freedom Trail, the Boston Public Library, the Public Garden, the Harborwalk, weekday State House tours, the Arnold Arboretum and Thursday evenings from 5 to 9 p.m. at the Gardner Museum all cost nothing.
Q. When is the 2027 Boston Marathon?
Monday, April 19, 2027, which is Patriots' Day in Massachusetts. The race finishes on Boylston Street in Back Bay.
Q. Can you do a Boston bucket list in winter?
Much of it. Fenway Park tours run every day of the year and the museums stay open, but the Swan Boats run only from mid-April to early September and the Harbor Islands ferries only from mid-May to mid-October.
Q. Where can you see all of Boston from above?
View Boston, on the top three floors of the Prudential Tower in Back Bay, has indoor and open-air decks. General admission starts at $32, and it is open daily from 10 a.m. to 10 p.m.