7 Best Sights in Gloucester, Side Trips from Boston

With white sand and dunes, Wingaersheek Beach is a well-protected cove with both a beach side and a boat side. The white Annisquam lighthouse is in the bay. The beach is known for its miles of white sand and calm waters. Make a required parking reservation online after Memorial Day through summer. The parking lot is accessible and beach wheelchairs are available on request. Amenities: food and drink; parking (fee); toilets. Best for: swimming; walking.

The Cape Ann Museum celebrates the art, history, and culture of Cape Ann. The museum’s collection includes fine art from the 19th century to the present alongside artifacts from the fishing, maritime, and granite-quarrying industries, as well as textiles, furniture, a library-archives, and three historic houses.

This beach has calm, waveless waters and soft sand, and is surrounded by grassy dunes, making it perfect any time of year. In summer (June, July, and August), it is lifeguard patrolled and wheelchair accessible, and there is a snack bar if you don't feel like packing in food. The restrooms and showers are also accessible, and you can pick up beach toys at the concessions. On weekdays parking is plentiful, but the lot fills by 10 am on weekends. In June, green flies can be bothersome. Amenities: food and drink; lifeguards; parking (fee); showers; toilets. Best for: swimming; walking.

Inventor John Hays Hammond Jr., credited with more than 500 patents, including remote control via radio waves, built this structure in 1926 to resemble a "medieval" stone castle. The museum contains medieval-style furnishings and paintings, and the Great Hall houses an impressive 8,200-pipe organ. From the castle you can see Norman's Woe, the rock made famous by Longfellow in his poem "The Wreck of the Hesperus." In July and August, unique "Spiritualism Tours" are an additional option on Thursday night (for an extra fee), with discussion of topics like the Ouija board, spirit photography, séances, and the science behind Spiritualism. Note: the museum is not wheelchair accessible. Parts of the grounds are free to visit.

Just as its name implies, this soft-sand beach that is half in Rockport, half in Gloucester is long, and it's also broad. It draws crowds from the houses that border it, particularly on weekends. Pay attention to the tide schedule, or you may find there's no beach to sit on. Cape Ann Motor Inn is nearby. Parking is very limited. Don't even think of parking on neighborhood streets if you don't have a town parking sticker—you will be towed. However, there is a lot on the Gloucester side. Amenities: none. Best for: swimming; walking.

On a peninsula within Gloucester’s working harbor, the town's creative side thrives in this neighborhood, one of the oldest continuously working artists' colonies in the United States. Its alumni include Winslow Homer, Maurice Prendergast, Jane Peterson, and Cecilia Beaux. While some venues stay open year-round, expect many to be closed in winter.

Consider a sail along the harbor and coast aboard the meticulously maintained 65-foot schooner Thomas E. Lannon, crafted in Essex in 1997 and modeled after the great vessels built a century before. From mid-May through mid-October the Ellis family offers two-hour sails, including trips that let you enjoy the sunset or music.