18 Unique Things to Do in Boston: A Local’s Guide

Updated for 2025

Discover Boston’s quirky side with unique experiences. From secret gardens to oddball museums and hidden eateries, these 20 activities reveal the city’s cool history and offbeat charm for locals and visitors.

Learn about the neighborhoods behind these activities in our Boston neighborhoods guide.

“For a unique Boston art museum experience, explore the Isabella Stewart Gardner Museum, a Venetian-style palace with a mysterious 1990 art heist,” says David, from My Travelation blog. Founded in 1903, this museum houses Gardner’s unchanged collection of paintings, sculptures, and tapestries, arranged as she intended. Visit in 2025 for new exhibits like “Waters of the Abyss” (Feb 27–May 25). Afterward, stroll the nearby Emerald Necklace, serene parks designed by Frederick Law Olmsted.

Boston’s Vietnamese community thrives in Dorchester and the South End, bringing rich coffee culture. At Phinista Cafe (96 Peterborough St, South End), a top Boston Vietnamese cafe, try the signature phin coffee, brewed through a metal filter for bold flavor. Pair it with a bahn mi, a crispy baguette with pickled veggies and grilled meat, for a unique brunch in this culturally diverse neighborhood.

Catch live jazz nightly at Wally’s Cafe, a South End gem at 427 Massachusetts Ave, near Berklee College of Music. This historic Boston jazz club, open since 1944, hosts talented students and local artists in a cozy, brick-walled space. Sip craft cocktails or local brews while enjoying the chill atmosphere, perfect for music lovers seeking a community vibe.

4. Explore Boston’s history and innovation on self-guided tours

Boston’s iconic tours blend history and innovation. The Freedom Trail, a 2.5-mile red-brick path, connects 16 historic sites like the Old State House. “It’s free to explore, with a water shuttle from Long Wharf to Charlestown Navy Yard for a subway fare,” says Michael Wenke of Revolutionary Story Tour. The Innovation Trail visits Harvard Yard and Kendall Square’s tech hubs, showcasing Boston’s role in AI and biotech. These Boston historic tours offer a unique journey through the city’s past and future.

Bodega (6 Clearway St, Back Bay), a hidden Boston sneaker store, hides behind a vintage Snapple machine that opens into a sleek boutique. “It’s not just shopping; it’s a peek into Boston’s underground culture with DJs spinning,” says Michelle McCormack of Secret Boston. Find rare sneakers and streetwear in this one-of-a-kind spot near The Newbury Hotel.

6. Brush up on your sports history

At The Sports Museum in TD Garden, explore Boston’s sports history with memorabilia from the Celtics, Bruins, and more. “It’s a hidden gem for fans,” says Sanjay of TD Garden Venue. Just steps away, relax at Pennyweight Hotel’s 155 on Portland bar (155 Portland St), serving craft cocktails and American fare. This Boston sports history stop is perfect for locals and visitors.

“To complete your Boston trip, wander the North End’s Italian charm,” says Kayla Crugnale of Pia Boutique. Hanover and Salem Streets brim with mom-and-pop shops like Cafe Dello Sport (308 Hanover St), Bova’s Bakery, and Florentine Cafe. Grab a pistachio iced coffee and explore Christopher Columbus Park’s waterfront views. This Boston North End Italian experience is a must.

8. Sample one of Boston’s famous lobster rolls

Neptune Oyster (63 Salem St, North End), a top Boston lobster roll spot, serves fresh seafood in a cozy setting. Choose a warm, buttery lobster roll or cold with mayo. “While waiting, stroll Hanover Street or visit EBO Grocery in East Boston for wine and provisions,” says Stefanie Finocchio-Durham of Root + Sky Wellness. This North End gem draws crowds for its quality.

9. Discover the North End off the beaten path

Beyond the North End’s tourist spots, find hidden North End Boston gems. “Skip crowded Paul Revere Mall for Charter Street Park, a quiet garden oasis,” says Chris of Boston Hidden Gems. Walk the Harborwalk for stunning waterfront views and benches. End with dinner at a family-owned Italian restaurant, a perfect way to soak in this historic district’s charm.

10. Fly amongst the trees on a treetop adventure

For a Boston outdoor adventure, head to TreeTop Adventures in Canton (30 min from Boston). Open spring through fall, this park offers zip lines, netting, and obstacle courses for all ages. Ideal for families or groups, it’s a thrilling escape. Check 2025 schedules at treetopadventure.com for bookings.

Cool off with our guide to Boston’s public pools.

11. Get lost in a sea of purple lilacs

Harvard’s Arnold Arboretum (Jamaica Plain) spans 281 acres with trails and gardens. “Visit for Lilac Sunday, likely mid-May 2025, to see 400+ lilacs bloom,” says Sacha of Sacha Eats. This Boston lilac festival is a spring highlight. Nearby, try Pikalo for empanadas or Blue Nile for Ethiopian fare.

12. Wander one of Boston’s most historic neighborhoods

Beacon Hill’s cobblestone streets and Federal-style homes ooze New England charm. “Grab coffee at Tatte Bakery (70 Charles St), snap a photo on Acorn St., and shop Charles Street,” say Michael and MacKenzie of Stay New England. End with a stroll through Boston Public Garden, a historic park with skyline views. A top Beacon Hill Boston attraction.m.

13. Get a taste for Boston’s beer 

Sip craft beers like Orange Line IPA at Turtle Swamp Brewing (3377 Washington St, Jamaica Plain), a community-focused Boston craft brewery. With a cozy taproom and local ingredients, it’s a welcoming spot for beer lovers. Try small-batch brews and soak in the neighborhood vibe.

14. Make your own Boston-inspired gourmet meal

Join Selfup cooking classes (19 Kingston St, Downtown) for a hands-on Boston cooking class. Learn New England seafood dishes or global cuisines from top chefs. “It’s a fun way to taste Boston’s food scene,” says a Selfup instructor. Enjoy your creations in a communal dining setting, perfect for foodies.

The Vendome Fire Memorial (Commonwealth Ave, Back Bay) honors nine firefighters lost in 1972. “Touch the sculpture for gratitude,” says Chris of Eat Walk Learn. At Charlestown Navy Yard, catch the USS Constitution’s sunset gun, a daily Boston naval history ritual at dusk (5–6 PM, seasonal).

16. Catch a show at the Boston Opera House

The Boston Opera House (539 Washington St) stuns with grand architecture and shows like The Nutcracker (check 2025 dates at bostonballet.org). “Dine at Faccia a Faccia or Contessa on Newbury Street, then walk through Public Garden to the theater,” says Elizabeth Brosseau of Carry On Only. A top Boston theater show experience.

17. Discover Boston’s spooky past on a haunted ghost tour

Haunted Boston Ghost Tours (nightly, hauntedboston.com) explore historic crime scenes and haunted sites. “Guides share eerie tales of restless spirits,” says Dan Seeger, tour manager. This Boston ghost tour 2025 experience through Boston Common and Old Granary Burial Ground thrills history fans.

18. Visit a holiday market

Snowport Holiday Market (100 Seaport Blvd, Nov–Dec 2025) transforms Seaport into a festive wonderland. Shop 100+ local vendors, including Lizzie’s Bakery for cupcakes and cake jars. “It’s a Boston holiday market 2025 must,” says a vendor. Enjoy twinkling lights and seasonal treats.

Looking for more seasonal fun? Check out Boston’s top summer events.