Best 141 things to do in Brookline, MA

Taste Central Square bites and explore mural-filled Graffiti Alley on a 2-hour weeknight walk

Taste french fries and pairings on a Harvard Square walking tour

Taste your way through Central Square murals and local restaurants

Charter a private yacht and cruise Boston’s waterfront with your group

Charter a 50-foot yacht for your private Boston Harbor cruise

Eat your way through Boston’s North End on a private guided tour

Eat your way through Boston’s North End with pizza, fresh mozzarella, pasta, and cannoli

Walk the North End and Boston Public Market with pizza, cannoli, and chowder tastings

Taste North End favorites and explore Boston Public Market on a private 3.5-hour walk

Walk Boston’s North End for pizza, beer stops, and Paul Revere history

Discover Colonial-era Lexington on a 90-minute guided trolley ride led by costumed historians.

Paddle Lake Cochituate with a single kayak rental in Natick

Pedal across Lake Cochituate with 1–4 hour rental options

Rent a stand-up paddleboard for a calm paddle on Lake Cochituate

Private sail for up to 6 guests beyond Marblehead Harbor

Private 4-hour sail from Marblehead Harbor for up to 6 guests

Walk Salem’s darker side with true crime and cemetery stories

Walk downtown Salem with a kid-focused guide and hear true Witch Trials stories

Hear Salem’s dark history with a local paranormal investigator

Enjoy a small-group, behind-the-scenes museum tour with expert docent and complimentary digital photos.

See authenticated pirate treasure from the Whydah shipwreck at Real Pirates Salem

Walk Salem’s Witch Trials sites in 1 hour with a guided group tour

Walk downtown Salem and trace 400 years of military service in 1 hour

Tour Salem’s Hocus Pocus filming locations, plus a movie ticket