Once you step off the beach in Gloucester, you’ll discover a community rich in heritage, food, and the arts. Here are a few of our favorite ways to enjoy this unique and dynamic city.
eat+drink
Tonno
The freshest of seafood meets Italian flavors in a warm and inviting atmosphere at this local favorite by restaurateur Anthony Caturano (also known for Lynn’s Blue Ox and Boston’s Prezza). 2 Main St., 978-879-4795, tonnorestaurant.com
1606 Restaurant
The restaurant inside the Beauport Hotel serves up seasonal flavors with unbeatable views. Sit in a cozy booth or pull up a stool at the recently renovated raw bar. 55 Commercial St., 978-491-5090, 1606restaurant.com
Cake Ann
This local favorite recently moved to the waterfront and expanded its operation, baking up a very wide selection of cupcakes, cookies, and pastries. 63 Rogers St., 978-865-4100, cakeann.com
Yella on the Water
Modern Mediterranean fare served overlooking the harbor. Sit in the airy dining room or on the breezy deck— either way, order the iced tea. 25 Western Ave., 978-491-5334, yellagrille.com
Virgilio’s
Enjoy the sounds of classic Italian crooners while you wait for a loaded sandwich on a fresh semolina roll, or browse the shelves of imported Italian provisions. 29 Main St., 978-283-5295, virgiliosbakery.com
Pastaio via Corta
Shop for handmade, small-batch pasta, including a rotating selection of seasonal ravioli and tortellini flavors, and everything else you need to complete your dinner, from olive oil to wine. 123 Main St., 978-868-5005, pastaioviacorta.com
shop+renew
Design of Mine
Affordable and eclectic clothing with bohemian flair is for sale alongside one-of-kind accessories handmade by shop owner Melissa Tarr. 33 Main St., 978-491-7495, designofmineshop.com
Goodlinens Studio
A delightful shop blending utility and beauty in its selection of linen towels, kitchen and bath goods, stationery, gadgets, and decor. 130 Main St., 978-515-7646, goodlinensstudio.com
Matthew Swift Gallery
Promising beautiful and intelligent modern art, the gallery runs a rotating series of exhibitions and keeps a carefully curated inventory available. 189 Main St., 978-491-7785, matthewswiftgallery.com
live+play
Cape Ann Museum and Cape Ann Museum Green
Featuring art and artifacts from Cape Ann history, the small museum offers a big cultural experience. Visit the new museum green for special events, outdoor sculpture, and rotating installations. Main campus at 27 Pleasant St., Green at 13 Poplar St., 978- 283-0455, capeannmuseum.org
Tompson Street Reservation
With more than 12 miles of trails available, hikers can challenge themselves to summit Eagle Rock, or take it easier and enjoy the woodlands and swamps. Parking areas Concord St., Bray St., and Fernald St., ecga.org/Property/Tompson-Street-Reservation
Gloucester Stage Co.
Enjoy a show at this small professional theater that packs a lot of talent into its summer schedule of original plays. 267 East Main St., Gloucester, 978-281-4433, gloucesterstage.com
Gabriel and Selma Kleimola Reservation
Wide, flat trails loop around scenic abandoned granite quarries and connect to the trail network in nearby Dogtown, for those looking for a longer walk. 49 Leverett St., ecga.org
Maritime Gloucester
The waterfront site includes a marine education center, aquarium with touch tanks, and new science center, as well as the chance to see how wooden dories are crafted. 23 Harbor Loop, 978-281-0470, maritimegloucester.org
Ravenswood Park
This network of wooded trails—from a wide, flat carriageway, to more hilly, rocky terrain—can make you forget you’re moments from the sea. Very dog-friendly. 481 Western Ave., 978-526-8687, thetrustees.org/place/ravenswood-park
Gardens at Stacy Boulevard
This long, narrow park along the harbor is home to the famous Man at the Wheel statue, the Gloucester Fishermen’s Wives Memorial, and dozens of garden beds that are kept in lush bloom by volunteers. Western Ave.
Rocky Neck
One of the country’s oldest working art colonies offers a pleasant stroll, beautiful scenery, and an array of quirky, colorful galleries and studios. Rocky Neck Ave., rockyneckartcolony.org