8 Hidden Gems Things to do in Cape Ann That You Shouldn't Miss

Also called the Beauport Sleeper-McCann House, this fantasy mansion of more than 40 rooms is perched on the rocks overlooking Gloucester Harbor.

Come visit and tour our craft distillery, the first legal distillery on the North Shore since Prohibition! See firsthand how fine hand crafted spirits are made in our beautiful copper pot Still. Learn how we ferment, distill, barrel age and bottle our Beauport Vodka, Knockabout Gin, Folly Cove Rum and Ryan & Wood family of Whiskies. All done on site. The tour, usually guided by Kathy or Bob Ryan, is free and lasts about an hour. Perfect for a quick stop before lunch. We are a hidden gem, just minutes from other Gloucester attractions. Scheduled Tours: Monday,Wednesday,Friday and Saturday, 10:00am and 1:00pm. Call for Private/Group Tours. Check our website for more information.

Connemara Bay Charters offers lobsterbake cruises, saltwater fishing, lobstering, and scenic charters in and around the waters off Cape Ann, Massachusetts (including Gloucester, Rockport, Manchester and Ipswich). The Connemara Bay is a 37-foot traditional, “Down East”-style Maine-built boat with plenty of deck space to accommodate up to six passengers. All charters are captained by Kevin O’Maley, a native of Gloucester with a lifetime of experience fishing, lobstering and boating in North Shore waters.

Windfall, our elegant 49-foot sailing vessel, is available for day or overnight sailing charters.We dock for the summer season (June–October) in historic Gloucester, MA, in Smith's Cove, within walking distance to the famed artist colony of Rocky Neck. Summer charters are also available out of Boston or any accessible New England port. Or, use Windfall as your floating B&B (Boat & Breakfast dockside) while visiting the lovely Cape Ann region. In autumn we head south to go sailing in the beautiful, sunny Bahamas from late February through May. Meet us at our base of operation, Abaco, Bahamas. Or, charter Windfall for island hopping anywhere in the Bahamas. We practice all state and local covid-19 sanitation guidelines.

Scramble across ledges scarred by the granite industry and examine tide pools teeming with marine life.

Hammond Castle Museum is now open for the season! The Museum is a 501(c)(3) non-profit organization and is listed on the National Register of Historic Places. It is not handicap accessible. The Museum’s architectural style is mix of medieval castle, French chateau, and Gothic cathedral. It was custom built to encompass Hammond’s private residence, laboratory and museum quality collection of architectural elements such as the facades of medieval shops and doorways from chateaus. Hammond’s extensive list of patents, and his work on radio control and on echo guided torpedoes for the military are also on display. It is available for weddings and private rentals.

Over 4000 wooden ships have been built on the banks of the Essex River since 1668. The Essex Shipbuilding Museum traces the evolution of traditional boat building through artifacts, photographs, hands-on exhibits and tour guides with deep knowledge of maritime and local history. Both guided tours and self-guided tours are available. Group tours and field trips can be scheduled. The School House building interprets ship models from the Smithsonian Institute.

Serving as a guide to ships entering the scenic and commercial Gloucester harbor from the Atlantic Ocean, this 36-foot tall cylindrical brick tower was built in 1832 and automated in 1986.