Boston Family-Friendly Road Trip: Visiting Nearby Gloucester Massachusetts

Looking to take a quick family-friendly day trip?  Gloucester, MA, a short drive from Boston, has a variety of kid-friendly activities.  Here’s a sample itinerary.

Breakfast: Sugar Magnolia’s is home to some of Gloucester’s best pancakes, in a sunny, family-friendly atmosphere in the heart of Main Street.

Morning activities

10:00 a.m. – 11:15 a.m. -Take a Lobstering Tour around Gloucester Harbor. Ever wonder how lobsters are caught? Captain Steve Douglas will show you how to pull lobster traps like real lobstermen do. The kids can even help with the haul – and catch their own 4-star dinner! 1 ¼ hour narrated tour of the Harbor. Tours are 1 ¼ hours and run at 10 a.m., 1 p.m., or 2:30 p.m.

Or if your children are comfortable on a sail boat (faster than the lobster boat, you’re riding fairly close to the water) for a longer tour:

10a.m. -12 p.m. – Take a relaxing sail aboard the Schooner Thomas E. Lannon. Breathe the clean salt air and feel the wind as it fills the schooner’s sails. The kids can help raise the sails and coil the ropes as you sail past lighthouses, scenic beaches and magnificent waterfront homes along the Harbor. This is a 2 hour sail, Kids are free on the Saturday 10:00-12:00 sail.

Lunch: The Pleasant Street Tea Company, 7 Pleasant Street, Gloucester, is a great place for families – wonderful sandwiches and baked goods, smoothies, and big boxes of toys and puzzles for the kids to play with while you’re there. It’s just off of Main Street and a few buildings down from rainy-day destination the Cape Ann Museum, an American art museum specializing in the rich culture of the Cape Ann area.

Afternoon activities

After lunch, visit the Maritime Heritage Center. The Gloucester Maritime Heritage Center lets kids learn about fishing in a way all kids understand – by holding lobsters, prickly starfish and spiny sea urchins in their own hands. Kids can sound a real foghorn, use a rope-tying machine to make their own ropes, see video of shipwrecks with treasure, and try on deep-sea diving helmets. Admission is only $2 per child.

Go on a beach glass hunt! Tiny Island Beach Glass on Main Street, Gloucester, provides pails and treasure maps to find secret stashes of ocean treasure: colorful beach glass. Bring your pieces in and the shop will make them into a necklace, pin or bracelet with personal meaning.

Aside from these activities, Gloucester’s Main Street is filled with shops that include clothing for kids & adults, jewelry, antiques, toys, wonderful cafes and restaurants.  A few favorites for kids: Toodleloos toy store, West End Sweets ice cream & candy shop, The Bookstore of Gloucester.

Dinner: If your family enjoys Mexican food, Main Street stalwart (since 1992) Jalapenos is an outstanding choice, with a fun atmosphere, terrific service, fantastic food and a children under 12 menu that runs just $5.95. Thinking more of seafood? Try The Gloucester House at 63 Rogers Street (parallel to Main Street) and enjoy regional seafood dishes with harbor views.

Photo of Gloucester Maritime Heritage Center courtesy of Massachusetts Office of Travel & Tourism via Flickr.