1. Follow in the footsteps of revolutionaries on the Freedom Trail
The Freedom Trail is the best introduction to Revolutionary War-era Boston. This 2.5-mile, red-brick path winds its way past 16 sites that earned this town its status as the Cradle of Liberty. Follow the trail on your own, or hook up with a free guided tour by the National Park Service (April to October). Departing from Faneuil Hall, the tours max out at 30 people, so arrive early to secure your spot. Outside of the tour season, you can download a map (thefreedomtrail.org) to use. Many of the sites along the trail are also free to enter.
2. Take a tour of the Massachusetts State House
Visit the Massachusetts State House, the so-called `hub of the solar system’ to learn about the state insect (the ladybug) and to pay your respects to the Sacred Cod. Free tours by Doric Docents (Monday through Friday) visit the ceremonial halls, the legislative chambers and the executive branch.
3. Sit in the Governor’s Pew in King’s Chapel
The stately Georgian architecture of King's Chapel contains a bell crafted by Paul Revere and the prestigious Governor’s Pew, where George Washington once sat. It’s a lovely setting for weekly noontime recitals (Tuesday). Admission is always free, but a $2 donation is recommended.
4. Eat lunch at Boston’s historic marketplace
Lunch is not free, but the history lesson is. Take a look around the Great Hall and listen to a ranger talk about historic Faneuil Hall and its role as market and meeting place. Then head to Quincy Market to take your pick from dozens of affordable food stalls.
5. Remember Paul Revere’s revolutionary ride from the North End
On the night of April 18, 1775, the sexton hung two lanterns in the steeple at the Old North Church to signal the impending march of British soldiers. The historic church is free to enter, though a $3 donation is recommended. Behind the church, a bronze statue of the patriot oversees Paul Revere Mall.
6. Experience a sailor’s life aboard the USS Constitution
The USS Constitution is the world’s oldest commissioned warship, and it is docked in the Charlestown Navy Yard. Navy officers lead free tours of the upper decks, where you will learn about her exploits in America’s earliest naval battles. You don’t need money, but you do need a photo ID.
7. Explore the fort and lounge on the beach at Castle Island
Castle Island isn't really an island, but a vast, green waterside park with amazing skyline views. The massive Fort Independence is open for exploration (and free tours). Otherwise, you can relax on the beach, fish from the pier or dip your toes into the chilly harbor waters.
8. Climb to the top of the Bunker Hill Monument
The landmark obelisk marks the site of the fateful battle in June 1775 that turned the tides of the War for Independence. Climb the 295 steps of the Bunker Hill Monument to the top for an impressive panorama of city, sea and sky. You’ll expend nothing but energy.
9. Learn about Boston’s fight against slavery along the Black Heritage Trail
On Beacon Hill, the 1.6-mile Black Heritage Trail explores the history of abolitionism and African American settlement in Boston. Download a map for a self-guided walking tour; or meet up with the free NPS tour (April to October), which departs from the Robert Gould Shaw Memorial.
10. Discover the city’s most magnificent architectural and intellectual landmark
The Boston Public Library was built as a `shrine of letters’ but it is also a temple of art and architecture. Free guided tours depart from the main entrance; or you can pick up a brochure and guide yourself around the stunning, mural-painted halls. The BPL also hosts author talks, musical performances and other free events.
11. Get a glimpse of Boston’s excellent art collections
This is the Athens of America, so you should probably check out the art. On Wednesdays after 4pm, admission to the Museum of Fine Arts is by donation (pay what you can). On Thursdays after 5pm, the Institute of Contemporary Art hosts Free Thursday Night.
12. See the birthplace of the 35th president at the JFK National Historic Site
John F Kennedy was born and raised in this modest clapboard house in Brookline, now listed as the JFK National Historic Site. Listen to Rose Kennedy’s reminiscence, as you peruse the furnishings, photographs and mementos that have been preserved since the Kennedys lived here.
13. Get the inside scoop on America’s oldest university
Students lead free historical tours of Harvard Yard, also sharing their own perspectives on student life. The one-hour tours departs from the Smith Campus Center. Space is limited, so arrive early during busy seasons.
14. Admire the magnificent home and gardens at Longfellow National Historic Site
For 45 years, Henry Wadsworth Longfellow lived and wrote poetry in this stately Georgian manor near Harvard Square. The Longfellow National Historic Site is open from May to September, and the mansion contains many of the poet’s personal belongings, as well as lush period gardens.
15. Enjoy open air entertainment at the Hatch Memorial Shell
The Charles River Esplanade is Boston’s backyard, a fine venue for picnics, bike rides and leisurely strolls. Even better, all summer long, the Hatch Memorial Shell hosts free events like outdoor concerts, family flicks and Dancing in the Park.
16. Hobnob with artists at SoWa First Fridays
From the former factories and warehouses in the South End, artists have carved out studios and gallery space. The SoWa Artists Guild hosts an open studio event on the first Friday of every month (6pm to 9pm). Come examine the art and mingle with the resident creatives.
17. Let your kids romp at the Boston Children’s Museum
From the Art Studio to the Construction Zone, the Boston Children’s Museum is fun for all. It’s not free, but `Target Fridays’ mean that admission is only $1 on Friday after 5pm.
18. Sneak a peek inside Fenway Park
If you can’t get tickets to the big game, you can still sneak a peek inside Fenway Park. The Bleacher Bar is accessible from the street, with a window looking onto center field. The bar gets packed during games, when there’s usually a waiting list for window seating.The view from inside the Bleacher Bar at Fenway Park. Image by Joy / CC by 2.0
19. Glide across the ice at Harvard Skate
Bundle up! Boston is full of opportunities for winter fun. Harvard Skate (facebook.com/HarvardSkate) is an outdoor ice rink where it’s free to skate, but you’ll pay $5 to rent skates.
20. Grab a cheap and tasty lunch from the Falafel King
Two words: free falafel. That’s right, Falafel King customers are treated to a free sample while they wait. If you’re looking for lunch, this hole in the wall is quick and delicious.
21. Sample Boston’s finest on a Samuel Adams Brewery tour
Head to Jamaica Plain to see the birthplace of America’s original craft beer. On the Samuel Adams Brewery tour, learn about the history of the company, witness the brewing process and sample the goods. By `goods’, we mean frothy lagers, refreshing pilsners and tasty ales. The suggested $2 donation is passed on to local charities.