How to Spend A Weekend in Gloucester

Read on Northshore here

Breathtaking beaches, fresh-caught seafood, and quaint oceanside villages—Gloucester and its surrounding towns on Cape Ann are the perfect spots for a weekend getaway. This insider guide to one of New England’s best summer hangouts will help you plan the perfect mini vacation—no matter your budget.

Where To Stay

Shea’s Riverside Inn & Motel $

Located on the scenic Essex river, this cozy spot is just a short drive from Gloucester’s beaches, and walking distance from Essex’s best restaurants. 132 Main St., Essex, sheasinn.com 

Cape Ann’s Marina Resort $$

Situated on our Best of North Shore (BONS) award winner for Best Marina, this stunning resort boasts waterfront views from every room and a glass-enclosed indoor pool.  75 Essex Ave., Gloucester, capeannmarina.com

Beauport Hotel $$$

If you’re really looking to splurge on a beach weekend getaway, book a stay at the Beauport Hotel. Sweeping views of the ocean, a fantastic bar and restaurant, and tastefully nautical décor make this decadent option worth every penny. 55 Commercial St., Gloucester, beauporthotel.com

Things To Do

Rockport’s Bearskin Neck 

This quintessential New England seaside town is a must-see for any Cape Ann visitor. Shop your way through the streets and take in breathtaking views of the Atlantic coast from the granite breakwater. Noteworthy shops include jewelry store Village Silversmith, Bearskin Neck Country Store, and Rockport Fudgery. Art lovers will enjoy the plethora of galleries, and Rockport’s Motif No. 1, a small red fishing shack that happens to be the most painted building in the world! Bearskin Neck, Rockport, bearskinneck.net

Gloucester HarborWalk

This walkway not only offers yet another opportunity to marvel at Gloucester’s scenic coastline, but offers a history lesson as well. The self-guided tour is marked with 42 granite posts delineating Gloucester’s rich history as a working seaport.  St. Peters Lane, Gloucester, gloucester.harborwalk.org

Cape Ann Museum

A blend of old and new Cape Ann-related artists featured at this museum are sure to delight any art lover. The fine art collection features the largest group of works by marine artist Fitz Henry Lane, as well as a rotating collection of exhibitions. 26 Pleasant St., Gloucester, capeannmuseum.org

Cape Ann Harbor Tours

Take the Lighthouse cruise for a two-and-a half hour boat ride that circles Cape Ann—the only boat tour to do so. Other services include a lobstering trip and a cruise along the Annisquam river. 66 Harbor Loop, Gloucester, capeannharbortours.com

7 Seas Whale Watch

Get an unforgettable look at the ocean’s gentle giants at this top-rated whale watching tour. Other common animal sightings include dolphins, sharks, sea turtles, seals, and a variety of ocean birds. 63 Rogers St., Gloucester, 7seaswhalewatch.com

Wingaersheek Beach

A trip to Gloucester wouldn’t be complete without a beach day. Relax on the sand, splash in the calm waters, or explore the tide pools and climbing rocks. During low tide, a sand bar is exposed for a relaxing beach walk. 298 Atlantic St., Gloucester

Good Harbor Beach

Another renowned Gloucester beach is Good Harbor Beach. Surrounded by sand dunes and salt marshes, this popular spot makes for a picture perfect beach day.  99 Thatcher Rd., Gloucester

What to Eat

Coffee and Breakfast

Two Sisters Coffee Shop $

Inexpensive and unfussy, this highly acclaimed breakfast spot is an easy choice. The homemade fish cakes are a great way to sample the local seafood. 27 Washington St., Gloucester

Sugar Magnolia’s $$

Featuring extensive breakfast, brunch, and lunch menus, this cafe in downtown Gloucester is sure to have something for everyone. 112 Main St., Gloucester, sugarmags.com

Brother’s Brew Coffee Shop $

In need of a pick-me-up during your Rockport shopping excursion? This Bearskin Neck café’s delicious donuts and coffee will satisfy any caffeine cravings. 27 Main St., Rockport

Lunch and Dinner 

CK Pearl $$

This BONS-winning downtown Essex spot serves elevated seafood and barbecue dishes with a side of salt marsh views. Creative cocktails like the hibiscus margarita and vodka-and-elderflower-based Beachwater add whimsy to the menu. 112 Main St., Essex, ckpearl.com

1606 Restaurant and Bar $$$

Oceanfront views, an extensive drinks menu, and plates like filet mignon and lobster gnocchi round out the upscale dining experience at the Beauport Hotel’s on-location restaurant. 55 Commercial St., Gloucester, beauporthotel.com

Roy Moore Lobster Co. $$

Enjoy fresh-caught New England delicacies like smoked salmon, clam chowder, and—of course—buttery, indulgent lobster rolls. 39 Bearskin Neck, Rockport

Short & Main $$

A daily changing menu of fresh oysters, pizza, and Italian favorites make this downtown Gloucester hotspot a delicious option—even for seafood haters! 36 Main St., Gloucester, shortandmain.com

Tacos Lupita $

If your idea of a perfect summer meal is a carne asada taco piled high with fresh pico de gallo, check out this inexpensive hidden gem. Pair your meal with a Mexican soda for an authentic, refreshing treat.  63 Washington St., Gloucester, tacoslupitagloucester.wordpress.com

Lobsta Land $$

Quirky and casual, Lobsta Land offers a vast variety of meals guaranteed to please any diner. 84 Causeway St., Gloucester, lobstalandrestaurant.com

Drinks 

My Place by the Sea $$

A massive martini list and a bloody Mary garnished with bacon-wrapped lobster makes the cocktail selection at this Rockport restaurant and bar one of the best in town. 68 Bearskin Neck, Rockport, myplacebythesea.com

Stones Pub & Eatery $

If you prefer a low-key ambiance and inexpensive, tasty drinks, try this downtown Gloucester watering hole. 242 Main St., Gloucester

The Franklin Cape Ann $$

A smokey negroni with mezcal. Prosecco accented by grapefruit and St. Germain. A dirty martini with bleu cheese-stuffed olives. If any of these pique your interest, check out The Franklin. 118 Main St., Gloucester, franklincapeann.com

Sweets

Tuck’s Candy & Gifts $

Since 1929, this sweet shop on Bearskin Neck has been a local favorite. Make sure to try their famed saltwater taffy, which comes in a myriad of delicious flavors. 15 Main St., Rockport, tuckscandy.com

Holy Cow Ice Cream Café $

Whether you’re craving a simple cone of homemade ice cream, an ice cream sandwich made with fresh cookies, or a sundae with all the toppings, this ice cream café is sure to hit the spot. 80 Pleasant St., Gloucester, holycowicecreamcafe.com