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Things To Do

Castaways Vintage Cafe

65 Main Street, Gloucester, MA 01930

The cutest coffee shop with a coastal feel. They have such good drinks and adorable merch!

Woodman's of Essex

119 Main Street, Essex, MA 01929

One of our favorite places! Best place to grab fried seafood and enjoy a cold beer. About a 10 min drive from Gloucester. They have ice cream as well :)

Long Beach Dairy Maid

147 Thatcher Road, Gloucester, MA 01930

A simple old school drive up ice cream window. A fun coastal drive from downtown Gloucester. A mix of soft serve and hard ice cream, enough choices to please anyone!

Holy Cow Ice Cream Cafe

80 Pleasant Street, Gloucester, MA 01930

If you know us, this is a pillar in our relationship. Truly the best ice cream around with unique flavors! No soft serve here but you will find something you love!

Wingaersheek Beach

Gloucester, MA 01930

This might look familiar from your fridge ;) A beautiful beach with light house views and that crisp New England air.

Cape Ann Lanes/Laneside Pub & Brewery

53 Gloucester Avenue, Gloucester, MA 01930

Love this old school bowling alley with candlepin! They have a full restaurant and bar as well. Perfect for a lowkey activity!

Rockport Candle Company & DIY Candle Bar

5 Bearskin Neck, Rockport, MA 01966

A quaint candle shop where you can make your own candles! This is in the heart of Rockport where you can stroll and enjoy this adorable village.

Virgilio's Bakery

29 Main Street, Gloucester, MA 01930

Bread of the fisherman! A wide variety of baked goods and sandwiches. Perfect to grab and go! Pairs well with Cape Ann olive oil ;)

Cape Ann Whale Watch

415 Main Street, Gloucester, MA 01930

This can be a fun activity if you are looking for a 3-4 hour event out on the seas!

Cape Ann Harbor Tours

66 Harbor Loop, Gloucester, MA 01930

Many different cruises, ranging from light house tours to lobster boat tours. Check out their website for all they offer!

Halibut Point State Park

Gott Avenue, Rockport, MA 01966

A beautiful outdoor activity if you're looking to get some steps in with water views!