10 Best Things to Do in Rockland (MA)

Rockland, a quintessential hardscrabble town on Massachusetts’ South Shore, is known for its rocky terrain, making it less suitable for farming. However, the 19th-century industrial boom fueled the town’s development, with industries like shoemaking and lumber taking center stage. Many of the factories from this era have since been repurposed into residential spaces and artists’ lofts, preserving Rockland’s historical charm. After World War II, Rockland transformed into a cozy suburb of Boston, offering family-friendly attractions, shopping, sports, and cultural activities. The town’s vibrant community spirit is evident in its bustling Union Street commercial district and several town-owned conservation areas, such as Ames Nowell State Park, which provide outdoor recreation opportunities.

Exploring Rockland’s Charm

Rockland Center

At the heart of Rockland lies Union Street, a thoroughfare stretching from north to south. This main artery is adorned with historic buildings, including the Holy Family Church (1896), First Congregational Church (1894), and the Rockland Public Library, a Beaux-Arts Carnegie library dating back to 1904. Further south, the street intersects with the Hanover Branch Rail Trail, surrounded by well-preserved houses from the early 19th century and a variety of shops, like Rockland Cycle. A notable residence here is the Deacon Reed House, showcasing the Queen Anne style with Federal details from its construction period around 1818.

Community Celebrations: Rockland Day and Fall Festival

Rockland’s community spirit shines during its annual events, such as Rockland Day, held over two days in mid-June. The celebration kicks off with live music at Rogers Middle School on Friday and continues with more performances, food, a beer garden, and children’s activities at Veteran Memorial Stadium on Saturday. The festivities culminate with a traditional fireworks display.

Another major event, the Rockland Fall Festival, takes place on Union Street in early October. This festival features live music, over 100 vendors, a petting zoo, pony rides, food stalls, local club demonstrations, and a candy drop. A beer garden showcases brews from more than 90 cellars, while the popular “Touch a Truck” activity allows children to explore the town’s service vehicles.

Rockland Farmers’ Market

Held bi-weekly through the fall at Hartsuff Park, the Rockland Farmers’ Market has grown significantly, now hosting nearly 50 vendors. Visitors can find fresh produce from the South Shore and southeastern Massachusetts, along with items like roasted coffee, craft beer, wine, sauces, honey, baked goods, and organic pet treats. The market also supports local artists and makers, offering handcrafted wood carvings, ceramics, and more. The market often coincides with the annual fall festival, adding to the lively community atmosphere.

Outdoor Adventures and Recreation

Hanover Branch Rail Trail

The Hanover Branch Rail Trail, also known as the Rockland Rail Trail, stretches for 7.8 miles, linking Abington’s Old Colony Railroad with Hanover Four Corners. This trail, originally opened in 1868, has been transformed into a paved shared-use path since the 2000s, offering a scenic route for walkers, cyclists, and runners. Plans are underway to extend the trail to the Drinkwater River in West Hanover, enhancing connectivity and accessibility.

George Anderson Rockland Town Forest

Spanning over 40 acres, the George Anderson Rockland Town Forest offers a tranquil escape with its beech, pine, oak, and cedar woods along French’s Stream. Visitors can explore the network of trails, featuring wooden bridges and boardwalks, some adorned with charming trinkets and uplifting messages. The forest connects to the Twin Ponds Trail, offering a longer, more immersive outdoor experience.

Magoo’s Ice Cream & Sandwich

Since its opening in 2007, Magoo’s Ice Cream & Sandwich has become a popular local spot, offering 40 flavors of hard ice cream from Richardson’s Farm, over 50 types of soft serve, specialty sundaes, frappes, and razzles. The venue also features an 18-hole mini golf course with water features and new lighting for evening play. The food menu includes classic fast-food options, making it a favorite for families.

Rockland Ice Rink

Rockland Ice Rink, open year-round, is a hub for ice sports, hosting games for competitive leagues like the Eastern Hockey Federation and Bay State Hockey League. The rink offers public skating sessions, stick & puck sessions (helmet required), and learn-to-skate classes for all ages. The Hockey Jump Start program teaches foundational skills, including skating techniques and puck handling, catering to both beginners and more experienced players.

Rockland Golf Course

Golf enthusiasts can enjoy 36 holes at Rockland Golf Course, set in a scenic landscape of pine and oak forests, rocky outcroppings, streams, and ponds. The Challenge Course is known for being the longest par 3 course west of the Mississippi River, while the Players Course offers a mix of par 3s and short par 4s, making it accessible to golfers of varying skill levels. The Sports Bar & Grille provides a relaxing spot to unwind after a game.

Twin Ponds Trail

Located near the site of a former Naval Air Station, the Twin Ponds Trail offers a glimpse into Rockland’s past. Accessible from Spruce Street, this trail winds through fields that once served as runways and past the two ponds that give the trail its name. Along the way, hikers can see historic stone walls, remnants of farmland, and rocky outcroppings. For a more extended hike, visitors can connect with the Thompson Pond trail, extending into neighboring Abington.

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