Cailey & KJ

Friday, October 3, 2025 • Gloucester, MA
154 Days To Go!

Cailey & KJ

Friday, October 3, 2025 • Gloucester, MA
154 Days To Go!

Things to Do

On Main Street

Minglewood Harborside

Picture of Minglewood Harborside
25 Rogers St, Gloucester, MA 01930, USA
(978) 281-0223

Waterfront dining with an oversized deck and retractable glass walls creates an alfresco experience both inside and out. Fresh, local seafood, creative sushi, and tavern favorites are complemented by refreshing cocktails.

Website

Tonno Gloucester

Picture of Tonno Gloucester
2 Main St, Gloucester, MA 01930, USA
(978) 879-4795

Inspired by coastal Italian cooking, Tonno has quickly become one of the best Italian restaurants in Gloucester, MA. Meaning tuna in Italian, Tonno hopes to blend delectable dishes from both land and sea. After all, no Italian dish is complete without a hearty helping of hand-made pasta.

Franklin Cape Ann

Picture of Franklin Cape Ann
118 Main St, Gloucester, MA 01930, USA
(978) 283-7888

Boisterous gastropub pairs inventive New American eats with craft cocktails in a sharp, dark space.


Jalapeno's Authentic Mexican Restaurant

Picture of Jalapeno's Authentic Mexican Restaurant
88 Main St, Gloucester, MA 01930, USA
(978) 283-8228

Gloucester's authentic Mexican Restaurant. Established in 1992 we take pride in serving only genuine Mexican recipes from Mexico City, central and southern Mexico. Dishes are prepared using only the freshest possible ingredients.

Golf Courses

Cape Ann Golf Course

Picture of Cape Ann Golf Course
99 John Wise Ave RT 133, Essex, MA 01929, USA
(978) 768-7544

Cape Ann Golf course features beautiful sweeping views of Essex conservation land - from the tidal marsh across Stavros Reservation and backside of Crane Beach to the ocean and beyond.

Family Favorite’s

Woodman's of Essex

Picture of Woodman's of Essex
119 Main St, Essex, MA 01929, USA
(978) 768-6451

Over 100 years ago on July 3rd, 1916, Lawrence “Chubby” Woodman (Cailey’s Great-Great Grandfather), at the humorous suggestion of a friend, fried up a few clams at his roadside stand in Essex, Massachusetts and the original New England fried clams were born, right here at Woodsman’s.

Mile Marker One Restaurant

Picture of Mile Marker One Restaurant
75 Essex Ave, Gloucester, MA 01930, USA
(978) 283-2122

Mile Marker One is a local’s favorite waterfront restaurant and bar located in Gloucester, MA. Situated in the heart of a working waterfront marina, our various dining spaces have been designed to capture the best panoramic views of the beautiful Annisquam River and marina life year round.