September brings the best of both summer and fall to Gloucester and Cape Ann. Warm days by the water meet the first signs of fall, creating the perfect backdrop for harbor cruises, scenic adventures, local art, waterfront dining, and some of the area’s most anticipated annual events.
From the iconic Gloucester Schooner Festival over Labor Day weekend to art exhibitions, ghost tours, and seasonal specials, there are plenty of reasons to plan a September getaway. Here are just a few highlights happening around Gloucester and Cape Ann this month:
This Month’s Events
Gloucester Schooner Festival
September 3-6: Celebrate Gloucester’s maritime heritage during the annual Gloucester Schooner Festival, when schooners from near and far gather in America’s oldest seaport for four days of waterfront festivities. Labor Day weekend events include Maritime Heritage Day, schooner deck tours, the spectacular Parade of Sail through Gloucester Harbor, and more opportunities to experience the city’s rich maritime traditions. Learn More >>
Painting Light with Water-Based Oils with Melody Phaneuf
Thursdays, September 3-24: Embrace the changing season and explore the art of painting color and light during this four-week workshop with local artist Melody Phaneuf. Held Thursday afternoons from 2:00-4:00 PM at her Gloucester studio, the small-group class introduces environmentally friendly water-based oils while helping participants explore color relationships and the effects of light. Artists of all experience levels are welcome, and space is limited. Learn More >>
Haunted Harborwalk
Thursdays-Sundays in September: Discover a darker side of America’s oldest seaport on Haunted Harborwalk, a 90-minute guided ghost tour through historic downtown Gloucester and along the harbor’s edge. Wander old streets and hidden alleys while hearing true tales of tragedy, mystery, and the supernatural, from the witches of Dogtown to ghostly soldiers and restless spirits said to linger throughout the city. Learn More >>
Spiritualism Tours by Candlelight at Hammond Castle Museum
Thursday Nights Through October: Explore the supernatural side of Hammond Castle Museum during this atmospheric 55-minute guided specialty tour. Learn about John Hays Hammond Jr.’s attempts to communicate with supernatural entities using a Faraday Cage and Irene Fenton Hammond’s extensive astrological writings, all while exploring the Museum’s dramatic Gothic-inspired architecture by the glow of handheld electronic lanterns. Learn More >>
Thrift the Runway at The Cut
September 13: Celebrate fashion with a purpose during Thrift the Runway, a Second Glance fashion show benefiting The Open Door’s local hunger-relief programs. Doors open at 6:00 PM at The Cut, with the show beginning at 7:00 PM and an after party from 8:30-10:00 PM featuring a sip-and-shop, designers, models, and a curated selection of secondhand clothing and accessories. This year’s finale will feature custom upcycled looks created by Massachusetts College of Art and Design alumni using materials from Second Glance. Advance tickets are required. Learn More >>
Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3
Through September 20: Discover how everyday materials can take on entirely new forms in Piece-by-Piece: The Art of Assemblage, Where 1 + 1 = 3 at Cove Gallery in Rocky Neck Art Colony. Featuring works by five Rocky Neck artists, the exhibition brings together wire, reclaimed wood, cardboard, hardware, rocks, toy figures, recycled flameworked glass, and more to create surprising three-dimensional works exploring the possibilities of assemblage. Learn More >>
Into the Garden: Lindy Saunders
Through September 27: Visit Charles Fine Arts for Into the Garden, Lindy Saunders’ first solo exhibition. Rooted in the relationship between nature and abstraction, Saunders’ paintings invite visitors to look beyond the recognizable flower and consider the garden as a memory, refuge, place of discovery, or world entirely of its own. Learn More >>
Tour de Greenbelt
September 26: Experience some of Essex County’s most beautiful landscapes on two wheels during Greenbelt’s 12th annual Tour de Greenbelt. Beginning at Cox Reservation in Essex, riders can choose from paved and gravel routes ranging from 25 to 50 miles, traveling through forests, meadows, farmland, and salt marshes while passing more than 50 Greenbelt-protected properties. After the ride, celebrate with food, live music, and fellow cyclists at Cox Reservation. Proceeds support land conservation throughout the region, and online registration is open through September 23. Learn More >>
Essex River Cultural District Festival
September 26: Head to the Shipyard at 66 Main Street in Essex for an afternoon celebrating the Essex River Cultural District. From 2:00-7:00 PM, enjoy local vendors, food, live music, a bounce house, fire trucks, farm animals, visit the Essex Shipbuilding Museum, and more during this family-friendly community festival. Learn More >>
Things to Do
North Shore Adventures
Experience Cape Ann from a new perspective with North Shore Adventures. Get out on the water and explore the coastline while taking in Gloucester’s beautiful scenery and maritime surroundings. Learn More >>
MAGMA (Movement Arts Gloucester MA)
Get moving during your Gloucester getaway with MAGMA (Movement Arts Gloucester MA), a welcoming movement arts center offering classes and programs for a variety of ages and experience levels. From dance and movement to creative community programming, MAGMA offers another way to experience Gloucester’s vibrant arts scene. Learn More >>
North Shore Arts Association
Discover generations of Cape Ann creativity at the North Shore Arts Association, one of the region’s longstanding cultural institutions. Visit the association’s galleries to explore exhibitions featuring works by local and regional artists and experience firsthand the artistic tradition that has drawn painters to Gloucester for generations. Learn More >>
Dining
1606 Restaurant & Oyster Bar
Take in sweeping Gloucester Harbor views while dining at 1606 Restaurant & Oyster Bar at the Beauport Hotel. Located right off the hotel’s lobby, the restaurant showcases coastal New England flavors, fresh seafood, cocktails, and more in a beautiful setting overlooking the water. Learn More >>
Virgilio’s
A locals’ favorite, Virgilio’s serves Italian specialties, sandwiches, breads, and more in the heart of downtown. Stop in for a classic St. Joseph sandwich, pick up something for lunch while exploring the city, or take home freshly baked Italian treats. Learn More >>
George’s Restaurant & Bar
Start your day with a hearty breakfast or stop in for lunch at George’s Restaurant & Bar, a longtime Gloucester favorite. With a welcoming neighborhood atmosphere and a menu of classic breakfast and lunch favorites, it’s a great addition to a day exploring downtown. Learn More >>
Shopping
Common Crow Natural Market
Stock up for a picnic, beach day, or cozy evening at your accommodations with a stop at Common Crow Natural Market. This locally loved Gloucester market offers natural and organic groceries, prepared foods, local products, specialty items, and plenty of provisions for your Cape Ann stay. Learn More >>
Michalak Fine Art
Bring a piece of Cape Ann home with artwork from Michalak Fine Art. Browse works inspired by Gloucester and the surrounding coastline and discover a unique reminder of your time on Cape Ann. Learn More >>
Juliet Lockwood Studios
Juliet Lockwood Studios is a vibrant creative space offering art, curated vintage clothing, distinctive outerwear, and statement party pieces. The studio also specializes in custom millinery, designing one-of-a-kind hats and headwear. Beyond fashion, Juliet also creates bespoke home textiles. Learn More >>
Stay on Cape Ann
Atlantic Vacation Homes
Cape Ann getaways aren’t just for summer. Settle into a vacation home from Atlantic Vacation Homes and enjoy more space to experience Gloucester during the quieter fall season. Properties are available for getaways throughout the season, including Cape Ann Plein Air, Halloween, and beyond. Book a stay with an arrival date through the end of 2026 and save $150 with code FALLSPECIAL150. Learn More >>
The Highliner Hotel
New England residents can save 15% on a stay at The Highliner from September 1 through March 31 with the code NESTAY when booking direct. The offer is available to residents of Connecticut, Maine, Massachusetts, New Hampshire, Rhode Island, and Vermont, with reservations paid in full at booking and non-refundable.
Guests can also book direct during the same period with code WELCOMEGIFT to receive late checkout and a welcome amenity, subject to availability. It’s a perfect excuse to experience Gloucester as the busy summer season gives way to quieter days around the harbor. Learn More >>
Cape Ann Motor Inn
Wake up just steps from the sand at Cape Ann Motor Inn, located directly on Gloucester’s beautiful Long Beach. Oceanfront accommodations and easy access to the beach make it a relaxing home base for a September escape, when Cape Ann’s coastline begins to settle into the quieter pace of early fall. Learn More >>
From schooners filling Gloucester Harbor to art exhibitions, outdoor adventures, fall events, local dining, and coastal stays, September is a wonderful time to experience Gloucester and Cape Ann!