Things to do over Labor Day weekend in Gloucester (Updated 2026)

Whale Watching Tour in Gloucester
You are guaranteed whale sightings on this whale watching tour out to Stellwagen Bank, a national marine preserve about 12 miles off the coast of...
$47

Guaranteed Sightings! 7 Seas Whale Watch is located in the heart of historic downtown Gloucester, MA and in one of the busiest parts of Gloucester...
$44

Explore the stunning Gloucester Harbor and Annisquam River on a guided kayak tour from Boston. Paddle past historic landmarks, catch a glimpse of the famous...
$129

Looking for a day trip from Boston by train? Step inside a medieval-style castle on the New England coast! The Hammond Castle Museum, built in...
$75

Explore Boston, Cambridge, Salem, Cape Ann, and more! This package covers Boston's iconic Freedom Trail (Old North Church, Faneuil Hall, & more), the Harborwalk, Salem...
$21.49

Get the full Massachusetts experience with this combo of walking and driving tours around Boston! You’ll find ten tours in one app - all highly...
$43.99

Recommended: Purchase one tour per car, not per person. Everyone listens together! Discover the natural beauty of New England’s most picturesque coastline with this narrated...
$14.29

