15 Best Things to Do in Rockland (MA)

The ancient city of Rockland on the southern coast was not ideal for farming due to its rocky terrain.

Instead, industry flourished here in the 19th century, with shoemaking and the timber trade. A few former factories have been converted into residential developments and artists' buildings.

Since the end of World War II, Rockland has become a convenient southern suburb of Boston, with a small but robust commercial district along Union Street, close to family attractions, shopping, sporting facilities, and culture.

Rockland has some protected city-owned property to enjoy the outdoors, the rail trail running through the center, and the secluded pond at Ames Noel State Park, just moments away.

1. Rockland Center

The city's main artery is Union Street from north to south, surrounded by grand public buildings, turn-of-the-century business parks, and some fine residences.

Some of the most impressive buildings are the Holy Family Church (1896), the First Collegiate Church (1894), the Rockland Public Library, and the Carnegie Fine Arts Library from 1904.

To the south, where Union Street intersects the Hanover Branch Railroad track, there are carefully preserved 200-year-old homes, as well as a row of shops, including Rockland Cycle (215 Union St), that serve the track.

A striking residence here is the Deacon Read House (ca. 1818), built in the Queen Anne style with pre-Federal details.

2. Rockland Day

The largest community event of the year wraps up over two days in downtown Rockland in mid-June.

Live music is the focus of the Rockland Day celebration, with a stage set at Rogers Middle School on Friday.

The event then moves to Veteran Memorial Stadium on Saturday with more live performances, great food, a beer garden, arts and crafts and all kinds of activities to keep the crowd entertained.

In the evening, the festival concludes with a traditional fireworks display.

3. Rockland Fall Festival

Rockland comes together for another big event later in the year, when the Rockland Fall Festival transforms Union Street for a day in early October.

With an array of live music, over 100 vendors, a petting zoo, pony rides, food vendors, demonstrations from local clubs and organizations, and a candy drop, there's a lot going on.

Adults will delight in the beer garden with over 90 cellars, while one of the best activities for the little ones is “Touch a Truck,” which showcases the city's fleet of service vehicles.

4. Rockland Farmers Market

Every two weeks during the weekend, Rockland holds a farmers' market that gets bigger every year. The location is Hartsuff Park, a mile or so northwest of downtown Rockland, where you'll find about 50 vendors a week on average.

And of course, there's a wealth of fresh produce from the South Shore and southeastern Massachusetts, plus freshly roasted coffee, craft beer, local wines, sauces, honey, baked goods, cocktails, and organic pet treats.

More than half of the vendors are local artists and makers, selling anything from fine wood carvings to ceramics. The Rockland Farmers Market in early October coincides with the annual Fall Festival.

5. Hanover Branch Rail Trail (Rockland Rail Trail)

The Hanover Branch Railroad opened in 1868, connecting Abington's Old Colony Railroad with Hanover Four Corners, 7.8 miles away, and becoming part of the New York, New Haven and Hartford Railroad later that century.

Industrial E. Perry was the driving force behind the line, as the trains served boot and shoe factories, but also carried passengers.

Since the 2000s, three miles of right-of-way between the Hanover/Rockland city line and North Abington has become a shared-use paved path.

The trail is ten feet wide and has well-defined footpaths where it meets roads. In 2022, funding was awarded to expand drinking water throughout West Hanover.

6. George Anderson Rockland Town Forest

Named after a dedicated local environmentalist who has maintained, maintained and improved the property for decades, Rockland Town Forest includes more than 40 acres of forest along French Stream.

Adjacent to suburban residential neighbourhoods, the plot features peaceful beech, pine, oak and cedar trees, which are explored through a range of trails.

It has sections of bridges and wooden walkways, and parts decorated with small ornaments, rock monuments, and elevation letters. For a longer hike, you can head north off Spruce Street and pick up the Twin Ponds Trail, which we'll talk about later.

7. Mango ice cream and sandwiches

This ice cream shop, a small, family-owned business, opened in Rockland in 2007 and features an 18-hole mini-golf course and plenty of outdoor seating.

Magoo's offers 40 different flavors of hard ice cream, sourced from the award-winning Richardson Farm in Middleton, Massachusetts. You can choose from more than 50 soft drinks, as well as specialty ice creams, frappes and raffles.

Meanwhile, the menu features comforting fast food dishes, from chicken fingers to cheeseburgers. The mini golf course features rocks and water features, is well maintained and newly lit for long hours on summer evenings.

8. Rockland Ice Rink

Rockland has a popular public rink, which is open year-round and hosts games for several competitive leagues, including the Eastern Hockey Association, Bay State Hockey League, and the South Shore Conference.

If you just want to get out on the ice, there are many public skating sessions and stick and puck sessions (helmets required) with additional periods during school breaks.

The Winterland Ski School here offers five ski classes per week, suitable for all ages from three years old to adults.

If you want to learn some hockey basics, there is Hockey Jump Start, skating skills such as forehand and backhand crossovers, as well as puck handling and in-game positioning.

9. Rockland Golf Course

You can play golf on 36 holes at this unique Rockland property, set in a majestic pine and oak forest with rock outcroppings, streams and ponds.

The Challenge Course here is the longest par 3 west of the Mississippi River. This test track had four sets of tees, with a course record of four below par. So when the par is 3, you will need every club in the bag.

The Players Course is a bit more suitable for less skilled players, and consists of 12 par 3s and 6 short par 4s.

Afterward, you can continue your tour at the Sports Bar & Grill, which serves sandwiches, flatbread pizzas, quesadillas, wraps, nachos and other comfort foods.

10. Twin Ponds Trail

From 1941 until the end of the Cold War there was a Naval Air Station on the line between Rockland and Abington.

You can enter this landscape from Spruce St just north of the Rockland Town Forest, and after a few steps you'll be in a huge field where the amphitheater once was.

Little traces of the facility remain today, and the main blue trail passes two ponds of the same name, as well as historic stone walls dating back to the time of its cultivation, and several rock outcroppings.

For a longer visit, walk the main loop and then head west to Abington along the blazed Thompson Pond Trail.

11. Company Theatre

For some live entertainment minutes away in Norwell, there's a beautiful non-profit theater that presents five large-scale shows a year in a permanent location.

Founded in 1979, Company Theatre has won numerous awards, including Moss Hart and IRNE Awards.

A typical season brings an audience of over 20,000 people, with first-rate performances, choreography, music, set design, lighting, costumes and staging.

Keep an eye on the schedule because in addition to these shows, there are also an annual celebrity series, concerts and four annual youth productions.

12. Ames Nowell State Park

You can access DCR's 700-acre property within minutes from Rockland with plenty of natural spaces to explore around Rockland.

Much of Ames Nowell State Park is taken up by the magnificent Cleveland Pond, which was built in the 1920s when owner Edwin Holmes dammed Beaver Brook to create a bird sanctuary and hunting ground.

There is a rich history in the woods surrounding the pond, where a maze of stone walls, two wagon bridges and a pair of quarries indicate 400 years of settlement.

People come to the pond to pick up string and fish for largemouth bass, and there are more than ten miles of paved and unpaved trails that lead west and south into the forest.

13. Starland Sportsplex & Fun Park

Near the city of Hanover there is a family entertainment center with a sports theme, which has been open since 1968.

In 2013, Starland underwent a major expansion to build a more than 100,000-square-foot sports facility, with eight wood courts, two grass courts and additional amenities such as a full-service bar, restaurant and café.

The Sportsplex is home to basketball, volleyball, soccer and pickleball leagues, while elsewhere there are plenty of classic family attractions.

You've got mini-golf, laser tag, bumper cars, an arcade, go-karts, and batting cages, plus a rock wall, a dark XD ride and several carnival rides.

14. Derby Street Shops.

Slightly north of Rockland is Hingham, an upscale shopping center. Located just off Route 3, Derby Street Shops features about 70 shops and restaurants designed in the style of a cozy New England town, with wooden storefronts and tree-lined sidewalks.

To give you an idea of the shopping scene here, you'll find Barnes & Noble, Francesca's, Whole Foods, Banana Republic, Lululemon, Gap, Allbirds, Anthropologie, J. Crew, and the Apple Store.

Derby Street Jobs' restaurants are on the casual side of things, including Chipotle, Legal C Bar and CAVA.

15. Barrett's Haunted Mansion

You never have to travel far along the South Shore to see some first-rate Halloween scares, and that's what Rockland, the best in nearby Abington, is all about.

Barrett's Haunted Mansion has been in operation for more than 30 years, and is known for its clever theme, intricately designed scenery, and enthusiastic performers.

When we put this list together, the story is about a chemical leak that turns into a pesticide factory.

There are a selection of experiences, including Devil's Night, which allows physical contact for added scares, and Lights On Tour, which takes you behind the scenes to check out set design, make-up and costumes in the cold. daylight