15 Best Things to Do in Rockland (MA)

An archetypal hardscrabble town, Rockland on the South Shore was never ideal for farming because of its rocky terrain.

Instead, industry boomed here in the 19th century with trades like shoemaking and lumber. A few of the factories from those times have since been turned into residential developments and artists’ lofts.

Since the end of WWII Rockland has become a comfortable southern suburb for Boston, well-served by nearby family attractions, shopping destinations, sports amenities, and culture, with a small but robust commercial district along Union Street.

To enjoy the outdoors in Rockland there are a few town-owned conservation properties, a rail trail that cuts through the center, and the secluded pond at Ames Nowell State Park, moments away.

1. Rockland Center

The town’s main artery is the north-to-south Union Street, which is flanked by grand public buildings, turn-of-the-century commercial blocks and some stately residences.

Some of the more impressive buildings are the Holy Family Church (1896), the First Congregational Church (1894), and the Rockland Public Library, a Beaux-Arts Carnegie library from 1904.

Further south, where Union Street is crossed by the Hanover Branch Rail Trail, there’s an array of neatly preserved houses dating back 200 years, as well as a lineup of stores, including Rockland Cycle (215 Union St), serving the trail.

One eye-catching residence here is the Deacon Reed House (c. 1818), in the Queen Anne style with earlier Federal details from the time of its construction.

2. Rockland Day

The biggest community event of the year goes down in Rockland’s center over two days in mid-June.

At the heart of the Rockland Day celebration is live music, with a stage set up at Rogers Middle School on the Friday.

The event then moves to Veteran Memorial Stadium on the Saturday with a packed schedule of yet more live performances, great food, a beer garden, arts & crafts and all kinds of activities to entertain wee ones.

In the evening the festival wraps up with the traditional fireworks show.

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.

There’s a lot going on, with a lineup of live music, more than 100 vendors, a petting zoo, pony rides, food vendors, demonstrations by local clubs and organizations, and a candy drop.

Grownups will be pleased with the beer garden, representing more than 90 cellars, while one of the top activities for youngsters is “Touch a Truck”, displaying the town’s fleet of service vehicles.

4. Rockland Farmers’ Market

Happening every other weekend through fall, Rockland has a farmers’ market that gets bigger with each year. The location is Hartsuff Park, a mile or so northwest of Rockland’s center, where you’ll encounter close to 50 vendors on an average week.

Naturally there’s a wealth of fresh produce from the South Shore and southeastern Massachusetts, as well as fresh roasted coffee, craft beer, wine from the region, sauces, honey, baked goods, mocktails, and organic pet treats.

As many as half the vendors are local artists and makers, selling anything from fine woodcarving to ceramics. In early October the Rockland Farmers’ Market coincides with the annual fall festival.

5. Hanover Branch Rail Trail (Rockland Rail Trail)

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

Industrialist E. Y. Perry was a driving force behind the line, with trains serving his tack and shoe factories, but also carrying passengers.

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

The trail is ten feet wide and has well-marked crosswalks where it meets roads. In 2022 funding was awarded for an extension across West Hanover to the Drinkwater River.

6. George Anderson Rockland Town Forest

Named for the dedicated local conservationist who secured, maintained and improved this property over decades, the Rockland Town Forest is more than 40 acres of woods along French’s Stream.

Bordered by suburban residential neighborhoods, this parcel has quiet stands of beech, pine, oak and cedar, explored via a knot of trails.

These have wooden bridges and stretches of boardwalk, and have sections adorned with little trinkets, rock monuments and uplifting messages. For a longer walk you can exit in the north at Spruce Street and pick up the Twin Ponds Trail, which we’ll talk about later.

7. Magoo’s Ice Cream & Sandwich

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

Magoo’s serves 40 different flavors of hard ice cream, sourced from the award-winning Richardson’s Farm in Middleton, MA. You can also choose from more than 50 kinds of soft serve, as well specialty sundaes, frappes, and razzles.

On the food menu meanwhile are comforting fast food plates, from chicken fingers to cheeseburgers. Scattered with boulders and water features, the mini golf course is well looked after and has new lighting for longer hours on summer evenings.

8. Rockland Ice Rink

There’s a well-regarded public rink in Rockland, open all year and hosting games for a number of competitive leagues, including the Eastern Hockey Federation, Bay State Hockey League and South Shore Conference.

If you just want to get out onto the ice there are several public skating and stick & puck sessions (helmet required), with additional slots during school breaks.

The Winterland Skate School here offers five learn-to-skate classes each week, catering to all ages from three-year-olds to grownups.

If you want to pick up some hockey basics there’s the Hockey Jump Start, teaching skating skills like front and back crossovers, as well as puck handling and in-game positioning.

9. Rockland Golf Course

You can play 36 holes of golf at this unique facility in Rockland, set in magnificent pine and oak forest, with rock outcroppings, streams and ponds.

The Challenge Course here is the longest par 3 west of the Mississippi River. There are four sets of tees on this testing track, with a course record of four under par. So while it’s a par 3 you’re going to need every club in the bag.

The Players Course is a little more accommodating for less accomplished players, and is made up of 12 par 3s and 6 short par 4s.

Afterwards, you can talk over your round at the Sports Bar & Grille, serving sandwiches, flatbread pizzas, quesadillas, wraps, nachos and other satisfying bites.

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 Rockland Town Forest, and after a few steps you’ll be in an immense field where the runways used to be.

There are few traces of the facility remaining today, and the main blue-blazed trail leads past the two namesake ponds, as well as historic stone walls from when this was farmland, and several rocky outcroppings.

For a longer visit you can walk the main loop and then head west into Abington along the red-blazed Thompson Pond trail.

11. The Company Theatre

For some live entertainment there’s a beloved non-profit theater putting on five large-scale productions a year at a permanent venue a few minutes away in Norwell.

Founded in 1979, the Company Theatre has earned numerous accolades, including Moss Hart and IRNE Awards.

A typical season brings in audiences of 20,000+ , with musicals comprising first-class performances, choreography, music, set design, lighting, costumes and direction.

Keep an eye on the schedule because as well as these shows there’s an annual celebrity and concert series, and four annual youth productions.

12. Ames Nowell State Park

To go with the ample natural space around Rockland you can reach this 700-acre DCR property in a matter of minutes from Rockland.

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

There’s rich history couched in the woods around the pond, where a labyrinth of stone walls, two wagon bridges, and a pair of quarries hint at 400 years of settlement.

People come to fish for chain pickerel and largemouth bass at the pond, and there are more than ten miles of paved and unpaved trails leading off into the woods to the west and south.

13. Starland Sportsplex & Fun Park

Close by in Hanover there’s a sports-oriented family entertainment center, open since 1968.

In 2013 Starland came through a major expansion, building a 100,000+ sq ft sports facility, with eight hardwood courts, two turf fields and host of complementary amenities like a full-service bar, restaurant and coffee shop.

This sportsplex is a venue for basketball, volleyball, soccer and pickleball leagues, while elsewhere you’ve got a ton of classic family attractions.

You’ve got mini golf, laser tag, bumper cars, an arcade, go karts, batting cages, as well as a rock wall, XD dark ride and a variety of carnival rides.

14. Derby Street Shops

There’s an upmarket shopping center a little way north of Rockland in Hingham. Just off Route 3, Derby Street Shops has close to 70 stores and restaurants in a setting designed like a cozy New England town, with clapboard storefronts and broad tree-lined sidewalks.

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

The eateries at Derby Street Jobs are on the casual side of things, with the likes of Chipotle, Legal C Bar and CAVA.

15. Barrett’s Haunted Mansion

You’ll never have to travel far on the South Shore for some high-quality scares at Halloween, and this goes for Rockland, which has one of the best in the area nearby in Abington.

Barrett’s Haunted Mansion has been running for more than 30 years, and is known for its smart theming, intricately designed scenarios and enthusiastic actors.

When we put this list together the backstory revolved around a mutating chemical leak at a pesticide factory.

There’s a choice of experiences here, including Devil’s Night, in which physical contact is permitted for extra terror, and a lights-on tour, in which you get to go behind the scenes to check out the set design, makeup and costume in the cold light of day.