Your Get-A-Way Guide to Rockport & Cape Ann
Your Get-A-Way Guide to Rockport & Cape Ann
Events:
September – Near The Rockport House
Rockport Exchange Farmers Market — Harvey Park, Rockport
Saturdays in September — 9:00 am – 1:00 pm
Fresh food, local vendors and a relaxed Saturday morning stop close to downtown Rockport.
Rockport Art Association & Museum Exhibitions — Rockport Art Association & Museum
Throughout September
Seasonal exhibitions, artist shows and gallery visits in one of Cape Ann’s most established art institutions.
Spiritualism Tours by Candlelight — Hammond Castle Museum, Gloucester
Thursday nights in September
Atmospheric evening tours at Hammond Castle Museum, perfect for guests looking for something memorable after a beach or harbor day.
October
Cape Ann Plein Air — Locations throughout Cape Ann
October 3–11, 2026
Watch artists paint the coast and visit galleries and art sales throughout the week. In Rockport, Nocturne Painting brings artists to Bearskin Neck on October 4 from 6:00–9:00 pm.
Rockport Harvest Fest — Downtown Rockport
October 17, 2026 — 11:00 am–5:00 pm
Spend a fall afternoon downtown at this free community festival. Rain date: October 18.
41st Annual Essex ClamFest — Shepard Memorial Park, Essex
October 24, 2026 — 11:00 am–4:00 pm
Browse local vendors and food offerings, then sample the clam chowder competition from noon–1:00 pm, while supplies last. General admission is free; chowder tasting requires a ticket.
☾⋆⁺₊🎃´₊⁺~ Halloween in Rockport & Nearby Salem 🕸️
Enjoy Rockport’s quieter seaside setting, then head to Salem for its month-long Haunted Happenings celebration. Salem’s October calendar includes a parade, ghost tours, markets and Halloween events. The MBTA Rockport Line serves Salem, making the train a useful option when October traffic and parking are busy. Check the schedule before you go.
Salem Haunted Happenings — Downtown Salem
Throughout October 2026
Browse the event calendar to choose a tour, performance, market or Halloween celebration that fits your visit.
Live Music
Shalin Liu Performance Center
Enjoy the warmth of live music this season with intimate performances set against breathtaking ocean views.
Music and dinner @ Feather & Wedge
Finely prepared local ingredients and music.
Art
Rockport 2nd Saturday Art Walk
New art walk events on the Second Saturday of every month. Enjoy an evening or art by the sea! 5–8 PM See you there!
The 15th Annual Flying Horse Outdoor Sculpture Exhibit
More than 50 temporary works on display. Free and open to the public seven days a week
Rockport Restaurant Favorites
The Fish Shack Bar & Restaurant
Small, unadorned eatery offering classic New England seafood standbys such as lobster & fried clams.
21 Dock Square, Rockport, MA
charleneporterfs.wixsite.com
+1 978-546-6667
Roy Moore Lobster Company
No-frills seafood eatery & market with outdoor waterfront seating only, plus a BYOB policy.
39 Bearskin Neck, Rockport, MA
www.roymoorelobster.com
+1 978-546-6696
My Place by the Sea
High-end, creative seafood creations plus romantic deck seating overlooking the ocean.
68 Bearskin Neck, Rockport, MA
myplacebythesea.com
+1 978-546-9667
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Little Sister
Bigger than a burger shoppe.
Burgers, dogs, fish & chips and more!
2 Doyle Cove Rd, Rockport, MA
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Hula Moon Cafe
A popular breakfast and lunch with harbor views.
27 Pleasant St, Rockport, MA
+1 978-546-2572
Fresco’s Seaside
Where great food, a serene beach ambiance, and cherished moments blend harmoniously to create an unforgettable dining experience.
18 Beach St, Rockport, MA
www.frescosseaside.com
+1 978-999-5449
Fleur Cuisine Harborside
Delicious food, local ingredients, and authentic bold flavors made from scratch!
1 T-Wharf, Rockport, MA
Fleur Cuisine Website
+1 978-309-5199
Feather & Wedge
We’ve created a space for you that celebrates Rockport’s history as a quarry town. Join us in our passion for good food, sourced from nearby fields and waters and prepared with care. Seasonal menu.
5 Main St, Rockport, MA
featherandwedge.com
+1 978-999-5917
Delisi’s Red Skiff
Snug breakfast & lunch cafe offering American comfort food favorites & local seafood specialties.
15 Mt Pleasant Pl, Rockport, MA
+1 978-546-7647
Brothers Brew Coffee Shop
A casual breakfast and lunch spot, where the locals hang out.
27 Main St, Rockport, MA
www.bracketts.com
+1 978-546-3775
Brackett’s Oceanview Restaurant
Casual, contemporary beachside venue offering classic New England surf ‘n’ turf plus water views.
25 Main St, Rockport, MA
www.bracketts.com
+1 978-546-2797
Bean & Leaf Cafe
Coffee & pastries as well as wraps & salads in a cozy daytime cafe with views of the harbor.
12 Bearskin Neck, Rockport, MA
rockportcafe.com
+1 978-546-7500
Sights in Rockport
Halibut Point State Park
Scramble across ledges scarred for eons by wind and wave, and examine tide pools teeming with marine life. Halibut Point State Park is a coastal area on 440 million year old granite offers spectacular views, wildflowers, visitors center.
Thacher Island
The Thatcher Island Twin Lights were the 11th and final lighthouses built by the British of Massachusetts Bay in 1771.
Bearskin Neck
Bearskin Neck, the heart of Rockport is a short stroll from the Rockport House. Come explore dining, art galleries, shopping and breathtaking seashore vistas.
Tours & Whale Watching
Rockport and Cape Ann offer lots of ocean activities including whale watching, tours, fishing, kayaking and more.
Gloucester Sights
Lighthouses of Cape Ann
Five iconic lighthouses stand tall along the Cape Ann coastline to protect seafarers from rocky shores and shoals.
Good Harbor Beach
Good Harbor is a favorite among Boston area beach goers. At low tide, one can walk out to Salt Island, while at high tide, one can enjoy body surfing or boogie boards.
Wingaersheek Beach
One of Massachusetts' best beaches features calm waters and protected dunes. Visitors can enjoy food, drinks, beach toys, and other amenities from the on-site concession stand, along with access to showers and bathrooms.
Hammond Castle Museum
Hammond Castle is located on the Atlantic coast of Gloucester. The castle, which was constructed between 1926 and 1929, was the home, laboratory, and museum of John Hays Hammond Jr.,
Exploring Gloucester
Gloucester Area Restaurant Favorites
1606 Restaurant & Oyster Bar
An oceanfront deck showcasing New England coastal dining at its best. Celebrate delicious Modern American cuisine prepared with fresh local ingredients
55 Commercial St, Gloucester, MA
1606restaurant.com
+1 978-491-5090
Oak to Ember
Coastal American cuisine dishes sourced from the Gloucester docks. A wood-fired grill and 500-gallon smoker add unique flavors
9 Rogers St, Gloucester, MA
www.oaktoember.com
+1 978-289-5859
Seaport Grille
Seaport Grille at Cruiseport Gloucester is located directly on the harbor with two decks for classic water-view dining.
6 Rowe Sq, Gloucester, MA
seaportgrillegloucester.com
+1 978-282-9799
Talise
Located in Annisquam’s Lobster Cove sits Talise, a seasonal restaurant serving a daily changing cuisine sourced from local farmers and fishermen.
33 River Rd, Gloucester, MA
www.taliserestaurant.com
+1 978-515-7814
Tonno Gloucester
Inspired by coastal Italian cooking, Tonno has quickly become one of the best Italian restaurants in Wakefield and Gloucester, MA.
2 Main St.
Gloucester, MA
tonnorestaurant.com
+1 978-879-4795