The Area
Whether you’re visiting to explore, let loose, or relax, Gloucester has it all.
Sights
Hammond Castle
Hammond Castle is a remarkable historic landmark located in Gloucester, Massachusetts, offering a unique glimpse into the past. Built in the early 20th century by inventor and playwright John Hays Hammond…
Thomas E. Lannon Sailboat
The Thomas E. Lannon is a historic sailboat moored in Gloucester, Massachusetts, celebrated for its rich maritime heritage and contribution to the region’s seafaring traditions. Named after the renowned fisherman and…
Cape Ann Whale Watch
Cape Ann Whale Watch offers spectacular marine experiences along the stunning coast of Gloucester, Massachusetts, allowing visitors to witness the breathtaking beauty of whales in their natural habitat. Renowned for its…
Wingaersheek Beach
Wingaersheek Beach is a stunning natural gem located in Gloucester, Massachusetts, renowned for its soft sands and crystal-clear waters. This picturesque beach offers a serene escape for families, nature lovers, and…
Good Harbor Beach
Good Harbor Beach is a popular and picturesque beach located in Gloucester, Massachusetts, known for its beautiful sandy shoreline and vibrant tide pools. This family-friendly destination offers a perfect setting for…
Shopping
Sage Floral Studio
Sage Floral Studio crafts bespoke floral designs that blend artistic flair with nature’s freshest blooms in Gloucester, Massachusetts. From lush bridal bouquets and elegant event arrangements to thoughtful everyday gifts, every…
The Brass Monkey
Once a Sears & Roebuck outpost, 85 Main Street found new life in 1975 when Jack and Linda Pallazola transformed it into a beloved sporting goods shop for athletes and families—a…
Dogtown Book Shop
Dogtown Books is a locally owned independent used bookstore that has served Gloucester since 1997. A favorite destination for both locals and visitors, it offers a carefully curated selection of used,…
Bananas
Bananas in Gloucester is your go-to spot for stylish vintage treasures at wallet-friendly prices. Discover distinctive clothing, unique linens, and meticulously curated retro gems that brim with character and history. Friendly…
80 Main Antiques & Ephemera
80 Main Antiques & Ephemera in Gloucester is a charming shop offering a curated mix of antiques, vintage collectibles, and historical ephemera. With ever-changing inventory sourced from local and regional estates,…
Main Street Arts & Antiques
Main Street Arts and Antiques is proudly run by an antique dealer who has deep roots in Gloucester and is the third generation of his family to do so. Over the…
Cape Ann Olive Oil Co
Cape Ann Olive Oil Co is a delightful artisanal shop in Gloucester, Massachusetts, dedicated to providing the finest selection of high-quality olive oils and balsamic vinegar. This charming store is known…
Turtle Alley Chocolates
Turtle Alley Chocolates is a delightful chocolate shop nestled in Gloucester, Massachusetts, renowned for its artisan confections and whimsical atmosphere. Specializing in handcrafted chocolates, the store offers an array of delectable…
Nichol’s Candies
Nichol’s Candies is a beloved confectionery shop located in Gloucester, Massachusetts, famous for its wide selection of homemade candies and treats. With a rich history and a dedication to quality, Nichol’s…
Surfari
Surfari is a vibrant coastal adventure shop located in Gloucester, Massachusetts, specializing in surf gear, outdoor apparel, and accessories for water enthusiasts. Known for its welcoming atmosphere, Surfari caters to surfers,…
Mark Adrian Shoes
Mark Adrian Shoes is a standout footwear destination in Gloucester, Massachusetts. Renowned for its curated selection of high-quality shoes, the store caters to diverse styles and occasions, offering everything from casual…
Masshole & Co. Pet Provisions
Masshole & Co. Pet Provisions is a dedicated pet supply store located in Gloucester, Massachusetts, known for its extensive selection of high-quality products for pets of all shapes and sizes. This…
Pop Gallery
For 16 years known as “Gloucester’s Emporium of Cool,” Pop Gallery is a stylish boutique in Gloucester’s historic West End offering a Coterie Collection of carefully curated clothing for men and…
Restaurants
Oak to Ember
Oak to Ember is a waterfront restaurant that revitalized a nearly 5,000‑square‑foot historic building in the heart of the city’s fishing, commercial, and tourist district, originally built as a fisherman’s union…
Alexandra’s Bread
Alexandra’s Bread at 265 Main Street in Gloucester is a warm, family-run bakery founded by Alexandra Rhinelander and Jon Hardy in 1996. Housed around a giant stone-lined oven, the bakery produces…
Seaport Grille
Located on Cruiseport Gloucester’s waterfront, the Seaport Grille offers two decks perfect for enjoying a traditional waterfront view while dining. Surf & turf, traditional American fare, Italian specialties, desserts from around…
Sang Lee Sushi
Sang Lee Sushi is a delightful restaurant in Gloucester, Massachusetts, celebrated for its authentic Japanese flavors and fresh ingredients. Known for serving some of the best sushi in the area, the…
DRIFT & WAVE Kitchen
DRIFT & WAVE Kitchen is a vibrant dining destination situated in the heart of Gloucester, Massachusetts, known for its inventive approach to cuisine and commitment to local flavors. This popular eatery…
Cove Cafe
Cove Cafe is a charming eatery situated in Gloucester, Massachusetts, offering a picturesque setting alongside delicious, freshly prepared dishes. Known for its inviting atmosphere, the cafe provides a menu that features…
Sclafani’s
Sclafani’s is a cherished Italian market and deli situated in Gloucester, Massachusetts, known for its authentic flavors and warm, family-oriented atmosphere. Offering a wide selection of imported Italian goods, fresh produce,…
Virgilio’s
Virgilio’s is a renowned Italian restaurant located in Gloucester, Massachusetts, celebrated for its warm ambiance and exceptional culinary offerings. Known for its fresh, homemade dishes, the restaurant features a diverse menu…
George’s Restaurant & Bar
George’s in Gloucester, Massachusetts, is a beloved local establishment known for its warm atmosphere and exceptional seafood. Nestled in the heart of this charming coastal town, George’s offers a variety of…
The Lobster Pool
Lobster Pool in Gloucester, Massachusetts, is a cherished seafood spot that embodies the essence of coastal dining. Set against the stunning backdrop of the Atlantic Ocean, this iconic eatery is renowned…
Lobsta Land Restaurant
Lobsta Land in Gloucester, Massachusetts, is a popular dining destination celebrated for its delicious seafood and welcoming ambiance. Known primarily for its fresh lobster dishes and classic New England fare, Lobsta…
Causeway Restaurant
Causeway Restaurant in Gloucester, Massachusetts, is a beloved culinary gem known for its fresh seafood and vibrant atmosphere. Established as a local favorite, the restaurant offers a diverse menu that highlights…
The Lobster of Gloucester
The Lobster of Gloucester is a highly regarded seafood restaurant that epitomizes the charm and flavor of coastal New England. Situated in the scenic town of Gloucester, Massachusetts, this eatery is…
Franklin Cape Ann
Franklin Cape Ann in Gloucester, Massachusetts, is a charming restaurant known for its delicious cuisine and inviting atmosphere. Committed to celebrating local flavors and ingredients, Franklin Cape Ann features a diverse…
Minglewood Harborside
Minglewood Harborside in Gloucester, Massachusetts, is a popular waterfront dining destination known for its delicious seafood and vibrant atmosphere. Offering a diverse menu that includes fresh fish tacos, gourmet pizzas, and…
Machaca
Machaca Gloucester is a vibrant culinary destination that brings the bold flavors of traditional Mexican cuisine to the heart of Gloucester. Known for its lively atmosphere and warm hospitality, Machaca Gloucester…
Tonno Gloucester
Tonno in Gloucester is a premier dining destination that blends contemporary Italian cuisine with fresh, locally sourced ingredients. Renowned for its exquisite seafood dishes and artisanal pasta, Tonno offers a culinary…
The Fisherman’s Wharf Food Truck
The Fish Truck in Gloucester, MA, is a popular food truck that brings the best of fresh seafood to the streets. Known for its vibrant flavors and innovative dishes, The Fish…
The Lobster Roller Food Truck
The Lobster Roller in Rockport is a beloved dining spot celebrated for its mouthwatering lobster rolls and fresh seafood offerings. Nestled along the scenic coastline, this charming eatery captures the essence…
Harbor 9
Harbor 9 is an exceptional waterfront restaurant located in Gloucester, Massachusetts, offering diners a unique blend of fresh, local cuisine and stunning views of the harbor. Known for its innovative menu…
The Cut
The Cut, which first opened to the public in 2024, is now well-known as the best place to enjoy quick food and live entertainment on the North Shore. Corporate parties, weddings,…
Long Beach Dairy
Visitors to Long Beach Dairy can enjoy the experience of sampling delicious homemade ice cream made from premium ingredients, perfect for warm summer days. With its dedication to quality and community,…
Holy Cow
Holy Cow Ice Cream Café is a beloved local spot specializing in super-premium homemade ice cream. This award-winning parlor, home to the North American Ice Cream Association’s Flavor of the Year,…
White Farm Ice Cream
White Farm Ice Cream is a charming ice cream shop located in Gloucester, Massachusetts, beloved for its rich, creamy treats and welcoming atmosphere. Known for serving up a variety of homemade…
Azorean Restaurant & Bar
Azorean Restaurant & Bar in Gloucester, Massachusetts, is a vibrant culinary destination that showcases the rich flavors of Portuguese cuisine. Renowned for its authentic dishes and welcoming ambiance, Azorean offers an…
Caffeine on the Coast
Cafe Sicilia
Caffè Sicilia weaves Italian café tradition with irresistible local charm. Savor expertly pulled espresso, buttery fresh pastries, and hearty sandwiches crafted from premium ingredients. Sink into a cozy nook for breakfast,…
Source Bakery
Source Bakery crafts masterful artisanal breads, pastries, and treats from high-quality, locally sourced ingredients in Gloucester, Massachusetts. Fresh croissants flake with buttery perfection, crusty baguettes boast crackling crusts, and indulgent cakes…
Lone Gull
Lone Gull Coffeehouse is a cozy haven blending rich, smooth coffee blends with nutty chocolate notes and the freshest-baked pastries. Linger in its living-room-like warmth over breakfast treats, lattes, or hearty…
