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Rachel & Jeffrey

June 8, 2024 • Gloucester, MA

Rachel & Jeffrey

June 8, 2024 • Gloucester, MA

Good Harbor Beach

99 Thatcher Rd, Gloucester, MA 01930, USA

Beachgoers must make a reservation for a parking spot at the beach. Reservations can be made up 10 days in advance on the Blinkay mobile app or Blinkay website. Reservations are required for non-resident parking at Good Harbor Beach, Wingaersheek Beach, and Stage Fort Park starting Memorial Day Weekend.

Wingaersheek Beach

Gloucester, MA 01930, USA

Beachgoers must make a reservation for a parking spot at the beach. Reservations can be made up 10 days in advance on the Blinkay mobile app or Blinkay website. Reservations are required for non-resident parking at Good Harbor Beach, Wingaersheek Beach, and Stage Fort Park starting Memorial Day Weekend.

Halibut Point State Park

Gott Ave, Rockport, MA 01966, USA
(978) 546-2997

Accessed through Halibut Point State Park, at Halibut Point Reservation, bird watchers get an eyeful from this low coastal shelf overlooking dramatic surf. The state park adjacent to the reservation surrounds the former Babson Farm Quarry, where granite was quarried at the turn of the 20th century and used to build thousands of streets, bridges, tunnels, monuments, warehouses, and buildings.


Today, the quarry is filled with ground water. Tidal pools harbor snails, hermit crabs, and sea stars. Weather-beaten bluffs make up a low rocky coastal shelf covered in bayberry, greenbriar, and shadbush, and during storms, waves crash over the rocky shore.

Cape Ann Museum

27 Pleasant St, Gloucester, MA 01930, USA
(978) 283-0455

Cape Ann Museum is an art and historical museum located in Gloucester, Massachusetts. Its collection and programming focuses on the artists and art colonies of Cape Ann, including the Rocky Neck Art Colony and the Folly Cove Designers.

Peabody Essex Museum

161 Essex St, Salem, MA 01970, USA
(978) 745-9500

About a 30-45 minute drive from Gloucester, but well worth the trip, the Peabody Essex Museum collections of the former Peabody Museum of Salem and the Essex Institute. At over 200 years old, PEM is one of the oldest continuously operating museums in the United States and holds one of the major collections of Asian art in the United States.


One of the top-ranked museums in North America, the PEM holds more than 840,000 works of historical and cultural art covering maritime, American, Asian, Oceanic and African art, Asian export art, and two large libraries with over 400,000 books and manuscripts.

Castle Hill on the Crane Estate

290 Argilla Rd, Ipswich, MA 01938, USA
(978) 356-4351

Tour the gorgeous Crane Estate, including the 59-room Stuart-style mansion, the Great House, which sits on Castle Hill at the the center of the 3,500-acre estate. The Crane family bequeathed the property to the MA Trustees of Reservations, who now steward 2,100 acres of the family’s 3,500 acres.


Advance passes for grounds admission to Castle Hill are suggested but not required. Having an advance grounds admission guarantees grounds admission for the day and time of your visit.

The Cultural Center at Rocky Neck

6 Wonson St, Gloucester, MA 01930, USA
(978) 515-7004

About a 10-minute drive from Gloucester, the Rocky Neck Artist Colony one of the oldest continuously operating art colonies in the United States. Dozens of working artists from painters, potters and textile designers to photographers and jewelry makers, display their work in Rocky Neck galleries during the summer months.


A variety of restaurants are available to suit every taste with live entertainment enhancing the ambiance in restaurants and bars on weekends. Experience an eclectic mixture of history and culture and a great place to stroll on a lazy summer day, to include in a day trip to the beach, or to enjoy a memorable meal.

Gloucester Fisherman's Memorial

The Fishermen's Memorial, Gloucester, MA 01930, USA

Located a block from downtown Gloucester, Stacy Boulevard parallels the Atlantic coastline and provides easy, scenic access to Stage Fort Park and its many top beaches. Walking the length of the half-mile promenade, you’ll pass Gloucester’s iconic Fisherman’s Monument (otherwise known as the “Man at the Wheel”) and cenotaph, as well as the Fisherman’s Wives Memorial statue. Cross over the working drawbridge, or simply watch marine craft such as lobster boats and sailboats make their way out to sea. Once you have finished exploring Stacy Boulevard, sample local culture and cuisine in downtown Gloucester, which is just a few minutes’ walk away. Metered street parking available.

Crow's Nest

334 Main St, Gloucester, MA 01930, USA
(978) 281-2965

Gloucester is America's oldest seaport, and you won't make it very far without seeing evidence of the pride in and respect for those lost at sea. If you're looking to catch up on Gloucester history (or if you're a fan of early 2000's George Clooney, Mark Wahlberg, Diane Lane, or John C. Reilly), we'd be remiss if we didn't recommend Sebastian Junger's 1997 book The Perfect Storm, and the 2000 movie of the same name. Afterwards, you can visit the real Crow's Nest, which is a beloved watering hole for fisherman and tourists alike!

Woodman's of Essex

119 Main St, Essex, MA 01929, USA
(978) 768-6451

A favorite, iconic spot for fried clams!

Great Marsh Brewing Company

99 Main St, Essex, MA 01929, USA
(978) 890-7827

True North Ale Company

116 County Rd, Ipswich, MA 01938, USA
(978) 312-6948

RiverWalk Brewing Co.

40 Parker St, Newburyport, MA 01950, USA
(978) 499-2337

Jim's Bagel & Bake Shoppe

34 Railroad Ave, Gloucester, MA 01930, USA
(978) 283-3383

Don’t be fooled by the Dunkin across the street - these are the best bagels and donuts in town!

Oak to Ember

9 Rogers St, Gloucester, MA 01930, USA
(978) 289-5859

Destino's Subs & Catering

129 Prospect St #3739, Gloucester, MA 01930, USA
(978) 283-3100

The Mill

121 Eastern Ave, Essex, MA 01929, USA
(978) 890-7139

Run by a friend of the family, and a great spot for breakfast, sandwiches, and baked goods!