Best 227 things to do in Winthrop, MA

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

Paddle Lake Cochituate together in a sit-on-top tandem kayak

Find Pre-Owned Watercraft and Paddling Gear

Paddle Lake Massapoag at your own pace in a single kayak

Paddle Lake Massapoag at your own pace in a canoe

Sail historic harbor waters with maritime insights and optional hands-on sailing

Introduce the family to deep-sea fishing with crew support for every age

Fish Gloucester’s banks with a seasoned captain and crew

Flow through low-impact yoga alongside playful baby fainting goats

Pet, brush, and feed treats to baby fainting goats

Hand-feed alpacas, learn about the herd, and capture farm photos

Crew an authentic WWII tank destroyer and feel the power on a short ride course

Drive a 1944 M4A3 Sherman with 1-on-1 instruction and time for photos

Climb aboard a 1944 M24 Chaffee tank for a 10-minute group ride

Climb aboard a 1944 M4A3 Sherman for a 10-minute ride for two

Learn to drive a 1944 M24 Chaffee light tank with one-on-one instruction

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

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

Rent an electric scooter in Central Square, Cambridge