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Places to See, Bites, & Drinks

Joe’s recommendations as an “out-of-towner”. Things to Do Around Gloucester & Beyond October is a beautiful time to explore coastal New England! In Gloucester, stroll the Boulevard and visit the Fishermen’s Statue, browse the Rocky Neck Art Colony, or enjoy chowder and a lobster roll by the harbor. Nearby Rockport offers charming shops and ocean views, while Salem buzzes with Halloween energy and historic sites. If you’re up for a drive, Boston and Portland, Maine make great day trips with stunning foliage and plenty to see. Don’t miss local favorites like apple picking at Russell Orchards, coffee at Lone Gull, or a beer tasting at True North Ale.

Lone Gull Coffee House

146 Main Street, Gloucester, MA 01930

For a wicked good latte.

Virgilio's Bakery

29 Main Street, Gloucester, MA 01930

For a true New England Deli experience. Joe's favorite - the St. Josephs Roll.

Caffe Sicilia

40 Main Street, Gloucester, MA 01930

Sweet tooth? Get your Italian cookies here.

Minglewood Tavern

25 Rogers Street, Gloucester, MA 01930

For a bite to eat and/or drinks.

Rockport Brewing Company

17 Railroad Avenue, Rockport, MA 01966

Joe's favorite brewery in the area.

Beauport Hotel Gloucester

55 Commercial Street, Gloucester, MA 01930

Upscale dining and great cocktails. Bar & Dining Room.

True North Ale Company

116 County Road, Ipswich, MA 01938

A bit of a drive from Gloucester/Rockport, but one of our favs.

Halibut Point State Park

Gott Avenue, Rockport, MA 01966

Visit the spot that Joe popped the question!

Gloucester Fisherman's Memorial

Gloucester, MA 01930

Sculpted by artist Leonard Craske and modeled after a local fisherman, the monument was completed in 1925 in honor of Gloucester’s 300th anniversary. The inscription at the base of the statue, from the Bible’s Psalm 107:23, reads: “They That Go Down to The Sea in Ships, 1623-1923”. Circling the monument are plaques with the names of those lost at sea from 1716–2001. Six of the most recent names on the tile are those of captain and crew from the Gloucester-based Andrea Gail, the fishing boat made famous in the book and film, The Perfect Storm (2000).

Bearskin Neck & Motif #1

Bradley Wharf, Rockport, MA 01966

Motif No. 1, the famous icon of Rockport, Massachusetts, is ready for its close-up. Artists, both experienced and novice, appreciate its lines and charm, while sightseers flock to photograph it every day. It’s the most painted building in the world. Bearskin Neck is a peninsula located on the coastline of Cape Ann in Rockport, Massachusetts. The location played a vital role during the War of 1812. Today it is a destination known for its shops and art galleries.

Gloucester Back Shore

45 Atlantic Rd., Gloucester, MA 01930

Drive along the beautiful back shore of Gloucester.

Pratty's CAV

10 Parker Street, Gloucester, MA 01930

Best Dive Bar in New England. Caitlin told me not to put this one on here - so hiding it at the bottom of the list :)