10 Family Friendly Spots in Gloucester, Massachusetts

Disclaimer: We visited Gloucester in October, the very end of their “peak season.” Gloucester is a wonderful place to visit any time of the year (those water views! that delicious seafood! outdoor recreation all year long!); however, many of the places on our list are closed from November-March, sometimes until May. We’re sharing our tips now so you can schedule a visit for the spring/summer and dream about the sunshine and fun all winter long. Our guess? You’ll want to keep coming back!

Known as “America’s oldest seaport”, Gloucester was the largest fishing port in America in the second half of the 19th century, and one of the top five ports in the world at that time. In addition to its contributions to the fishing industry, Gloucester also produced granite in nearby quarries as well as a thriving art community. Founded in 1623, the city is less than one hour north of Boston, directly on the Atlantic Ocean. Gloucester is one of four communities (Essex, Rockport, and Manchester-by-the-Sea are the other three communities) that make up the Cape Ann district.

My family visited Gloucester as a child (remember, I’m originally a Bostonian) but I had not visited in years when I read about a few places (here and here) that made Yankee Magazine’s Best of New England lists. My list of must see spots grew when I started reading more on DiscoverGloucester.com. I knew we needed get into town this year.

DiscoverGloucester.com is a great resource for “charting” a trip to the area. There are comprehensive lists of lodging options (from motels and hotels, to inns and bed and breakfasts, to campgrounds and vacation rentals) to lists of activities for every hobby and interest (both indoor and outdoor!) and plenty of special events each month. There are four visitor centers around town that make getting in person help easy , as well as plenty of ways to get around town- check here for more options.

It’s worth noting that Gloucester locals love their hometown. In every, single place we visited, we were greeted by friendly, enthusiastic people who were eager to share their stories, their history, and what makes Gloucester special to them. Being from Boston, I’ve always been proud to be New Englanders, but Gloucester raises the bar just a little higher. 

10 Must Visit Spots in Gloucester:

1. Stage Fort Park is the location where Agawam Indians arrived from the west over 10,000 years ago in search of fish. In the mid 1600s, the first permanent settlement of the Massachusetts Bay Colony was Stage Fort Park. Today, it’s a 25 acre park, part of the Essex National Heritage Recreation Area that includes two beaches, a dog park, tons of walking trails, and plenty of amenities for the whole family. Check here for a calendar of bandstand concerts and farmer’s markets dates. Travel Tips: Restroom facilities are located in the Visitor Center. There is a parking fee during peak summer season.
Kids will love the playground (replica ships! a lighthouse! climbing walls! swings!), baseball fields, and tennis courts.
Adults will love the Visitor Center with helpful guides and plenty of print materials for reference. Check here for hours.

2. Cape Pond Ice , the “coolest guys around”, will have you looking at ice with new found respect! Founded in 1848, Cape Pond Ice sells over 2,000 tons of ice to fishermen, businesses, and individuals each year. Take a tour of the facility to learn the history of the company and how ice was “harvested” and “preserved.” Tours, which typically last 45 minutes, are offered June through August five days a week. Check here for more information. Travel Tips: The facility (and tour) is not handicap accessible and strollers are not allowed. There are restrooms on site. Be prepared for the smell of fish- you’re at thee spot for fishing vessels to load up before they go out to sea.
Kids will love the film clips from Frozen and explanation of the ice tools used in the film, as well as the chance to throw snowballs (even in the middle of summer!) in the first floor Ice House. This was one of our children’s favorite spots of the trip!
Adults will love touring the facility, learning how a 335 pound- 40 gallon ice block is created, and checking out the ice sculptures in season.

3. Beauport, the Sleeper-McCann Home was built by interior designer Henry Davis Sleeper in the early 1900s. He lived in the 42 room “summer cottage” until his death in the 1930s, when the McCann family purchased it and lived there until 1942. The home was then bequeathed to Historic New England, which now oversees the property and the 10,000+ objects in the collection. Today, the home and gardens are open to the public through tours offered from May- October. Check here for more information and ask when Marie is giving tours- she was engaging, funny, and really connected with our children (and never once winced or jumped when our children came dangerously close to touching or bumping into something). Travel Tips: Guests are required to wear cloth booties over footwear (which the tour provides) to protect the flooring- wear sneakers or flat soled shoes. The home is not handicap accessible. Restrooms are located in a cottage outside the main home near the small gift shop. I would not recommend this tour for toddlers- too many temptations to touch and there are narrow spaces and stairs. Elementary school children will love the scavenger hunt and the quirky stories about the owners. Again, catch a tour with Marie.
Kids will love the secret doors and passageways, looking for hidden mirrors in every bedroom, finding 19 George Washington portraits and busts, the Ben Franklin game room, and costumes from the mid 1900s. 
Adults will love the pink kitchen with original cutlery and dishes, all FIVE dining rooms (the green one was jaw droppingly stunning!), the mariner’s room with a display of navigational tools, and the gorgeous water views from dozens of rooms.  This was my favorite spot of the trip!

4. Hammond Castle Museum is the former home of Dr. John Hammond, a famous scientist credited with with over 400 patents. He built the home in the late 1920s, originally on 7 acres, on the waterfront. An admirer of the medieval and gothic design, he imported many architectural elements from Europe. Hammond wanted the home reserved as a museum, and opened it to the public while he was still living in it in the late 1930s. Today, the castle is open for tours May through September and is open on weekends in October for Haunted Halls of Darkness. Travel Tips: The museum is not handicap accessible and I would not recommend it for toddlers- too many things to touch and many narrow staircases. Our elementary aged children loved the tour and found our guide Linda to be engaging and full of fun trivia. Wear comfortable shoes. There is a small gift shop and restrooms near the main waiting room (the women’s restroom has the best view in the whole castle!)
Kids will love peeking in the dungeon where poorly behaved guests where rumored to have been set for a “time out”, the courtyard with the 8’ deep pool where Hammond routinely went swimming ( jumping from the second floor hallway!), the “whisper” dome ceiling in the library where you can actually hear your voice change (try it!), and the Gothic bedroom where Walt Disney was a frequent guest (he even premiered Fantasia at the castle!).
Adults will love the Great Hall with 65’ ceilings and one of the largest, privately owned organs in the world (there are 7,400 pipes hidden in the walls!), the hand painted ceiling tiles imported from Spain in the dining room, one of only 15 claviharps in the world located in the library (try the whisper thing, too!), and the French village facades imported from Europe that line the indoor courtyard. 

5. The Cape Ann Museum celebrates the extensive art community of the area throughout the past three centuries. Almost all of the collection has been gifted to the museum, mostly by family members of the artists. A special exhibit highlighting the works of Winslow Homer is on display through November 2019- more information here. Travel Tips: The museum is fully handicap accessible and has plenty of restrooms. Children will be most interested in the Activity Center on the lower level, but older kids will enjoy many highlights throughout the museum. I would not bring the toddler crew just yet. The museum participates in reciprocity programs- check here for the list- and is open throughout the year, except Mondays, check here for hours. There is a coat room and lockers for bags and backpacks, as well as a gift shop, located next to the admission desk. Docent led tours are offered twice a day and are included in admission fee. I highly recommend taking a docent led tour- our docent Ed Becker had plenty of funny stories about artists and pointed out special details in many of the pieces of art. Our children were very engaged (when Ed was leading the way!)
Kids will love the Activity Center on the lower floor (book nooks, a little house, a replica canoe, and plenty of arts and crafts activities), the diorama of the Gloucester Harbor, the Fresnel Lens (the light from the south tower lighthouse on Thatcher Island) and the “Character Cards” located throughout exhibits, which help children learn about many of the subjects of various paintings. The Winslow Homer exhibit highlights pieces that would most interest children with “CAM is for Kids” stickers on the placards.
Adults will love the collection of Fitz Henry Lane painting from the 1800s, the Folly Cove textile designs exhibit, and the collections of furniture and sculptures from several centuries. 

6. Seven Seas Whale Watch tours are the #1 rated activity in town- and for good reason! Three to four hour tours (offered twice a day April through October) explore the Stellwagen Bank National Marine Sanctuary region and promise the site of whales. We never would have guessed just how many whales (over a dozen humpback whales) and ocean sunfish dolphins we would see and just how close we would get (check the photos- there is no zooming!). Staff will narrate throughout parts of the tour and share the history and geography of the area as well as explain the backgrounds of various species. They’ll will also come around to each part of the ship to share maps and visit with guests. There isn’t a bad seat in the house (but see tips below) and most tours spend 90-100 minutes watching the whales (it takes 45-50 minutes to travel in and out of harbor to various locations for the best whale sightings). Check here for the schedule. Travel Tips: Dress warmly and wear comfortable shoes. Guests may bring bags with clothing and snacks. The on board snack bar sells candy, snacks, drinks, and beer. There are restrooms on board the ship. There are two levels for sitting: the lower level has indoor tables and benches as well as outdoor benches and the upper level is open air with perimeter benches. In case of seasickness, stay outside towards the back of the boat. The staff is incredibly attentive and helpful- don’t hesitate to ask questions or voice concerns. 
Everyone will love the fresh air, the friendly staff, and the site of WHALES up close!

7. Boat cruises if you prefer a more intimate, or shorter, boat cruise around Gloucester. We did not have enough time to personally take a tour, but there are three boats I had researched so much I thought it was worth including on our list.

  • Schooner Adventurer is a National Historic Landmark, built in nearby Essex in 1926, and one of only three surviving Schooners built to travel the Grand Banks. Adventurer is docked at Maritime Gloucester (see #8 on our list) and visitors can take a community sail aboard Adventurer- more information here.

  • Schooner Thomas E Lannon is a 65 foot schooner that offers two hour, daily public sails during the summer and weekend public sails in May, September, and October. There are also special sunset music sails in the summer and Kids-Sail-Free Saturday mornings- more information here.

  • Schooner Ardelle, like the Lannon, is a restored Burnham-built schooner that can fit up to 50 passengers. It also operated out of Maritime Gloucester and is available May through October for 90 minute to two hour sails. More information on schedules and rates here.

8. Maritime Gloucester is an indoor museum with an outdoor aquarium that will engage children of all ages. It’s the perfect spot for the toddler set, but older children will still enjoy the exhibits, many of which have interactive touch screens. The outdoor aquarium features local species of sea life, like the rare blue lobster, during the summer months. There are also several special programs and events offered throughout the summer- check here for updates. Travel Tips: The museum is handicap accessible and there are restrooms inside the center. Limited street parking is located in front of the center, but more space is available in nearby lots. Leave time to walk the pier and watch the boats and schooners coming in and out of the port. A large gift shop is located at the admission room.  More information on hours here. Note: the Sea Pocket Aquarium closes in early October through April.
Kids will love the touch tanks in the aquarium (there’s a marine biologist on site to guide and share information about every creature) and the toddler room with plenty of pretend stations, puzzles, and games.
Adults will love learning about the identification, tagging, and tracking of whales in the area, and the real world time weather, which shares forecast from around the world.

9. Sargent House was the home of sea merchants and their families for over a century. The Georgian style home was originally built in the late 1700s for Judith Sargent Murray, a well known advocate for women’s rights. A large addition was built in the early 1800s and today, both floors are open to the public and include parlors, bedrooms, and exhibition spaces of decorative arts and furniture. Part of the tour includes the opportunity to see paintings by John Singer Sargent, a member of Judith’s family. Travel Tips: Guided tours are offered on the weekends from Memorial Day through mid October (check here for more information) and usually last one hour.  The first floor of the home is handicap accessible on first floor. There are public restrooms on the first floor.
Kids will love comparing the difference between girls and males growing up during the 1800s and the collection of shoes and witch bottles (found in the walls of the house!) It was a tradition for families to leave old shoes and witch bottles (filled with hairs and clippings) as a way to ward off evil spirits for the new owners of a home.
Adults will love the design elements of high Georgian architecture. There are several collections of porcelain and china pieces, as well as period furniture donated back to the home from families who lived there after Sargent.

10. Harborwalk for the best views from every angle in town. The 1.2 mile path traverses through town between The Gloucester House and Stage Fort Park. Make sure to stop at the Fisherman’s Memorial (famous for the statue and  sobering list of fishermen who died at sea) and the Fishermen’s Wives’ Memorial. The walk is defined by 42 granite pillars which tell the stories of important people and events of Gloucester’s history. Bookmark this link, which has a list of public restrooms open during business hours. If you are looking for more outdoor fun at the water, check out Good Harbor and Wingaersheek Beaches, both accessible to the public and with facilities that include restrooms, showers, and lifeguards. More information about public beaches here.

Getting around town: Gloucester is accessible via the Boston T (subway). Take the Rockport purple commuter line from the North Station in Boston to Gloucester Depot. The town is easy to navigate via car and very pedestrian friendly (who says all Massachusetts drivers are rude?). There are municipal lots on Roger Street and Middle Street which charge $5 for 10 hour parking and most street meter parking is 2 hours for $1.  Click here for a printable map of parking options and click here for a printable walking map. During peak summer (June through mid September) there is a trolley service around the downtown area that has a nominal charge- more information here. Bookmark this list of public restrooms open during normal business hours. 

Eating Local: We had the opportunity to explore several different establishments, but for a more comprehensive list, click here. Our recommendations:

  1. Minglewood Harborside for large portions, several gluten free choices, at least 12 sushi options, tons of open space for families, and attentive service.

  2. Virgilio’s for Italian pastries and the St. Joseph’s sub (locals order ahead of time to avoid the lines). Grab some homemade sauces and oils to bring home. Note: Vigilio’s is closed on Sundays.

  3. Sugar Magnolia’s for a massive list of omelettes and other breakfast favorites (and super yummy hot chocolate- they even has a raspberry version!) Note: Sugar Magnolia’s is closed on Mondays.

  4. The Gloucester House for downtown water views and great seafood. Make sure you try the cornbread they bring to the table- so good! The restaurant is walking distance to many shops, museums, boat tours, and the Harborwalk path.  And if you see Lennie, whose family has owned the restaurant since it opened in 1957, ask him to pull up a seat- he’ll be glad to share local folklore and history.

  5. 1606 Restaurant at the Beauport Hotel for outdoor seating on the waterfront and unique takes on traditional favorites (scallops with carrot puree and a death by chocolate cake that’s made by the in house pastry chef were our favorites). The wood paneled walls, cozy leather booths, and stunning views are the perfect ambience for date night and special celebrations. Children are welcome and the menu received two thumbs up from our kids. The outdoor patio has a large outdoor fireplace, and plenty of heaters and fleece blankets at every seat when the weather gets cooler. 

  6. Cape Ann Brewing Company for over a dozen in house beers on tap, great pub favorites, and a casual outdoor patio.

Staying Local: We were hosted by The Vista Motel, which has some of the best views in town- it’s worth getting up to see the sunrise over Good Harbor Beach. There is a heated pool and plenty of outdoor space with a beautiful lawn for games and rolling down the front hill. The morning breakfast room has a great lending library and tons of board games. The continental breakfast was way more than we’re used to- fresh pastries and bagels, fruit, yogurt, and lots of hot coffee and cold juices. Several rooms are pet friendly. Note: The Vista is closed November through March.

The Beauport Hotel, which opened in 2016, is directly on the waterfront with breathtaking views of the ocean. There are almost 100 rooms and suites available, many appointed with balconies and fireplaces. Other amenities include is a rooftop pool, beautiful indoor and outdoor dining (see our note about 1606 Restaurant above), a large bar, adorable gift shop, and plenty of cozy nooks and crannies to relax near a warm fireplace. In warmer months, guests can relax on the beach or take a bicycle for a ride around town. Check here for special packages, especially for the “off season.”

Disclaimer: My family was hosted by Discover Gloucester for the weekend. All opinions expressed are my own.