Close out the season with a coastal getaway on the scenic shores of Gloucester—our editors rounded up the top spots to stay, indulge and play.
At Hammond Castle Museum, curious travelers can explore rooms housing ancient artifacts and architectural elements, walk along the picturesque grounds and admire views of the Atlantic shoreline.
Welcome to historic Gloucester, where the quaint streets, serene harbor and scenic beaches tell a tale of maritime history and community pride.
WHERE TO EAT
Seaport Grille
As summer gently fades into autumn, grab a table at one of two waterfront decks on Gloucester Harbor and savor dishes like Ipswich clams. The salty breezes and sounds of the ocean will be welcome dining companions. 6 Rowe Square,seaportgrillegloucester.com
Short & Main
At Short & Main, taste the bounty of the region with plates like seared yellown tuna and fresh oysters. 36 Main St.,shortandmain.com
Talise
Indulge in tuna crudo or lobster at Talise on Annisquam’s Lobster Cove. With breathtaking waterfront views and a daily changing menu sourced from local purveyors, this family-run restaurant is a must. 33 River Road,taliserestaurant.com
WHERE TO STAY
The Beauport Hotel
Beauport Hotel
At this luxury oceanfront hotel, enjoy the seasonal rooftop pool and bar, beach cruiser bikes, an outdoor fire pit, direct beach access and the award-winning 1606 Restaurant & Oyster Bar. 55 Commercial St.,beauporthotel.com
Ocean House Hotel at Bass Rocks
This historic hotel, perched on the rocky shores of Cape Ann, has welcomed guests for over 100 years. Start your morning with a swim in the heated pool overlooking the stunning coastline. 107 Atlantic Road,oceanhousegloucester.com
WHERE TO SHOP
Jane Deering Gallery
Discover JDG, where contemporary art meets the rich heritage of Cape Ann. The gallery features national and international artists as well as established Cape-based artists. 19 Pleasant St.,janedeeringgallery.com
Local Colors Artists’ Cooperative
Welcome to Massachusetts’ oldest Artists’ Cooperative, where art enthusiasts can shop original art in various mediums, such as handpainted oils and fused glass. 121 Main St.,local-colors.org
M/N Contemporary Art
Visit downtown Gloucester’s newest gallery space, M/N Contemporary Art. This gem features work from the dynamic Vanessa Michalak, Rebecca Anne Nagle and afiliated artists. 20 Pleasant St.,mncontemporaryartgallery.com
FOR DRINKS
The Salted Cod Arthouse
A favorite among locals, the Salted Cod Arthouse features an extensive wine and beer list perfectly paired with small bites like pan con tomate. 53 Rocky Neck Ave.,saltedcodarthouse.com
1606 Restaurant and Oyster Bar’s seafood towers are a must-try.
1606 Restaurant and Oyster Bar
End a perfect September evening with cocktails on 1606’s patio overlooking seaside vistas. Guests can enjoy sips like the Lost Sailor with Leblon Cachaça, Domaine De Canton, falernum, pineapple and ginger ale. 55 Commercial St.,1606restaurant.com
WHERE TO HIT THE TOWN
The Cut
Gloucester’s ultimate entertainment destination, the Cut welcomes guests to spend the night listening to a live band while enjoying drinks in the gastro pub. 177 Main St.,thecutlive.com
DRIFT
Whether dining on the outdoor patio or inside DRIFT’s open-air layout, this spot oers a rustic yet upscale atmosphere complete with live music, local microbrews, custom-crafted cocktails and an extensive whiskey selection. 3 Main St.,driftgloucester.com
CULTURAL EXPERIENCES
Hammond Castle Museum
Visit the Hammond Castle Museum, where a blend of medieval castle, Gothic cathedral and Renaissance French village architecture transport you to another time. 0 Hesperus Ave.,hammondcastle.org
Sail out of Gloucester Harbor with Schooner Adventure.
Schooner Adventure
Hop aboard a beautiful 122-foot historic fishing boat and experience a sailor’s life from 100 years ago, helping the crew raise the sails or enjoying the stunning coastline. 23 Harbor Loop,schooneradventure.org
HIDDEN GEM
Enjoy an excursion to Dog Bar Breakwater Lighthouse.
Dog Bar Breakwater
Do as the locals do in Gloucester with a visit to Dog Bar Breakwater Lighthouse. Walk to the end of the 2,250-foot granite jetty, with views of the ocean and the Boston skyline on one side and Gloucester Harbor on the other. Gloucester Harbor,lighthousefriends.com
Photography by: CARIN MACNAMARA; COURTESY OF BRAND; KRAIG ANDERSON
