Best 262 things to do in Gloucester, MA

Bring your own drinks for a shared tiki boat cruise

Explore seasonal farm pop-ups, classes, and community events

Unwind with a gentle outdoor yoga flow alongside grazing alpacas

Meet, feed, and stroll with fainting goats on a farm trail

Walk wooded farm trails alongside adult fainting goats

Customize a private fishing or whale watch charter on a 70–90 ft boat

Fish at night with a family-run crew, with rod and reel rental included

Trace campus history, pranks, and architecture from MIT to Harvard Square

Trace April 19, 1775 with a licensed guide, from Old North Church to Bunker Hill

Walk Salem’s witch-trial sites and uncover its maritime past

Ride Boston’s Emerald Necklace on a 15+ mile guided bike tour

Rent an electric scooter in Central Square, Cambridge

Diagnose your scooter issue on a quick video consult

Test ride the Hiboy S2 scooter from a Cambridge showroom floor model

See fall foliage on a 1.5-hour Boston Harbor cruise with a gourmet picnic lunch

Cruise Boston Harbor and enjoy a fall brunch buffet aboard Northern Lights

Hear live ghost stories on a 90-minute Boston Harbor night cruise

Take in Boston Harbor’s history on a narrated midday cruise

Immerse yourself in Boston's Freedom Trail chronicle with a small-group, storyteller-led walk.

Trace Boston’s Jewish immigrant story through Beacon Hill’s North Slope and West End

Trace how Boston’s streets, shoreline, and infrastructure have evolved

Walk Back Bay’s Victorian landmarks and uncover Boston’s architectural legacy

Trace the engineering feat that transformed Boston's Back Bay

Trace Boston’s gay and lesbian history on a private guided walk