15 Best Things to Do in Pembroke (MA)

On the South Shore, about 25 miles south of Boston, Pembroke is a town on the North River, abounding with water, at marshes, brooks and a patchwork of large natural ponds.

Every spring, alewife herring migrate through the town, from Massachusetts Bay, along the North River, and up those smaller watercourses to their spawning grounds at Oldham and Furnace ponds on the west side of the town.

This has always been an important event in Pembroke, going back to before colonization, when the Wampanoag and the Massachusett called the area “Mattakeesett”, meaning “place of much fish”.

You can observe the migration in Pembroke around April, but at any time of year there’s a lot of natural beauty around the town, in towering pine forest, dark hemlock groves and a rare freshwater tidal marsh miles from the ocean.

1. Herring Run Historical Park

Right on Herring Brook, this historic park is a prime place to watch the alewife making their annual migration upstream to their spawning grounds in Furnace and Oldham ponds.

This fascinating natural spectacle normally takes place in April, and has been aided by the Pembroke Herring Fisheries Commission, which works year round to ensure the run is clear of obstacles.

At Herring Run Park the brook can be as shallow as six inches, so once you adjust your eyes it’s easy to spot the foot-long fish on their journey.

On the south side, at the end of Littles Ave you can access the Bicentennial Nature Trail, running through mostly pine forest and freshwater marsh for about half a mile, passing historic stone walls.

2. Wildlands Trust – Willow Brook Farm Preserve

Upstream from Herring Brook Park, this Wildlands Trust Preserve contains one of Southeastern Massachusetts’ most varied and interesting inland natural areas.

Here at the confluence of the Herring and Pudding brooks you can observe a rare type of freshwater marsh, affected by the tides despite being 11 miles from the ocean.

Along the three-mile trail system you’ll come to an observation tower, with an all-encompassing view of the Herring Brook valley.

What will strike you about these vistas is the total absence of development on the horizon. This lack of human encroachment enhances the water quality of the North River, aiding the annual herring run.

3. Wildlands Trust – Tucker Preserve

You can visit a magnificent stretch of the Indian Head River at this preserve, sitting west of Luddam’s Ford Park, which we’ll talk about a little later.

At the Tucker Preserve as you travel westwards, the character of the Indian Head River changes from a serene reservoir by the dam, to a deep gorge.

This wild scene can be admired from a high ridge wrapped in hemlock forest, in the kind of landscape more associated with western Massachusetts or New Hampshire.

Across the river here are the vestiges of the 19th-century Waterman Tack Factory, while lichen-coated stone walls are a reminder of a more distant agricultural history.

4. Pembroke Town Green

The heart of Pembroke for more than 300 years, the Town Green and surrounding center of Pembroke are set in a large, open landscape with mature trees and civic buildings at wide intervals.

The sense of openness is underpinned by the enormous, rolling Center Cemetery on the west side. On or near the green you’ve got the Town Hall, Pembroke Public Library, the Town Recreation Department, and a playground for little ones.

There’s a bandstand on the green for outdoor events, including concerts in summer. On the north side is the museum for the Pembroke Historical Society, made up of two adjoining one-room schoolhouses, dating to the mid-19th century and relocated to this site in 1952 and 1968.

5. Oldham Pond (Pembroke Town Landing)

One of the goals for that annual herring migration is this 235-acre natural pond, straddling the Pembroke-Hanson line.

At the turn of the 20th century Oldham Pond became a sought after location for summer homes, and has loose rows of lakefront homes on all of its shores.

In the last few years Pembroke has put a lot of work into revitalizing its public beach at Pembroke Town Landing on the eastern shore.

There are new ADA-compliant facilities including a bathhouse with snack bar, to go with a large spread of sand and a swimming area with lifeguards on duty late June through Labor Day.

One reason to swing by the Town Landing, at any time of year, is for the dreamy sunsets that can be enjoyed from this part of the shore.

6. Luddam’s Ford Park

With a blend of natural splendor and intriguing human history, this park has two parcels, one on the Pembroke bank of the Indian Head River, and the other on the Hanover bank to the north.

Pembroke has the larger of the two, composed of open meadow and forest next to a dam that powered The Clapp Rubber Works in the late 19th century and early 20th century.

This was the largest facility of its kind in the United States, and it’s not hard to find the remnants in the woods by the trail.

In the spring the fish ladder here is another great location for spotting alewife wriggling upstream. If you’re patient you may even see animals like ospreys, minks and foxes that prey on the fish.

7. Dairy Twist

Originally opened in 1994, this popular ice cream stand at 580 Washington St (Route 53), has been run by the same family for more than 20 years now.

Two things that set Dairy Twist apart are the generous portions and the mind-boggling variety of flavors. At the time of writing there were more than 60 flavors of hard ice cream alone.

These run the gamut from simple like vanilla and chocolate, to the likes of cotton candy, heath bar, cake batter and sea salt caramel truffle.

There’s also an array of limited-time flavors, including a choice of pumpkin spice-infused flavors in fall. Added to that you’ve got a huge menu of toppings, sundaes, soft serve flavors, sorbets, frappes, floats, and ice cream pies.

8. Soundcheck Studios

A tucked-away industrial complex in Pembroke is the unlikely location for a world-class rehearsal facility and live music venue.

Once you arrive, everything suddenly makes sense, and this intimate but well-equipped venue shines as one of the best places to watch a live show on the South Shore.

The schedule is busy, with performances at least several nights a week, for a chance to check out touring acts or artists from the region making waves. You can come for open mics on Mondays, there’s a well-stocked bar, and all shows are served by local food trucks.

9. Pembroke Arts Festival

A fixture of the local cultural calendar since 1968, the Pembroke Arts Festival celebrates the many artists and artisans in Pembroke and around the South Shore.

Held in mid-August, the venue for this three-day event is normally the Town Green, but recent editions have also taken place at Hobomock Elementary School.

At the core of the festival is a juried artist competition, with awards in a long list of categories including oils, pastel/drawing, color photography and many more.

For nascent masters there’s a young artist show, and you can also shop for something unique at the festival’s juried craft exhibit.

10. Hidden Hollow Farm

Maybe the best way to experience Pembroke’s wooded rural scenery is on horseback. This can be done via Hidden Hollow Farm, a small private farm, keeping ten horses and maintaining almost 20 acres of outdoor space and two miles of trails for rides.

There are lessons for all levels, from learn-to-ride programs for beginners to jumping and dressage at dedicated arenas.

The farm also offers summer camps and birthday parties, but if you’d just like to spend an hour on a gentle horse in the woods you can organize a trail ride.

This experience starts with grooming and saddling to get to know your horse, and then you’ll be taught the basics at the arena, before heading out on the trails.

11. Pembroke Friends Meetinghouse

Something to ponder at the intersection of Washington St and Schoosett St, is a Quaker church dating back more than 300 years.

Now in the care of the Pembroke Historical Society, the earliest elements of the Pembroke Friends Meetinghouse date to 1706, with enlargements made in the 19th century.

The church was in use until 1876, when its members started in New Bedford or Sandwich. In the 1700s and 1800s, many of Pembroke’s most prominent citizens were Quakers.

The building is rarely open to the public, but you can peek through the window to observe the divided layout, with women sitting on one half and men on the other.

12. Adah F. Hall House

Close to Herring Run Park at 52 Barker St is an historic First Period house owned by the Pembroke Historical Society.

The Adah F. Hall House, thought to date back to the 1680s, is withdrawn from the road down a long drive, and has a delightful setting with grassy fields hemmed by mature woods.

The history of the property can be traced back to the initial land grant by Myles Standish in the 17th century, and its earliest owner was a Quaker who owned a sawmill on Herring Brook.

You can see the interior during the society’s open house days, or organize a guided tour at other times by appointment.

13. Grand Old Fish Fry

As sure as the running of the herring, there’s a small festival to celebrate this event every spring. The Grand Old Fish Fry dates back more than 40 years, and traditionally takes place on the first Sunday in May.

This is the main fundraiser for the Pembroke Historical Society, aiding with the upkeep of historic landmarks like the Pembroke Friends Meetinghouse and the Adah F. Hall House.

There’s a schedule of activities at Herring Run Park, including duck races, live music, children’s activities like face painting and balloon modeling, and an annual lunch.

In the early days herring was on the menu, and this has been replaced with the likes of fish cakes, burgers and hot dogs.

14. Pembroke Country Club

Set in tall pine groves, this championship par 71 golf course first opened in 1973 and has undertaken a lot of work in recent years to open up the layout to improve playability.

Pembroke Country Club has a reputation for its long par 4s, five of which are more than 420 yards, posing a unique challenge for players of all standards.

As well as the course itself, the accompanying facilities have been revamped, including the pro shop, function halls and the grille, which has some lovely vistas over the course from its patio.

If you want to limber up before your round, or just improve your swing, there’s an all-grass driving range.

15. Bay Circuit Trail

Pembroke is on the southern third of a 230-mile trail arcing through Boston’s outer suburbs from Plum Island in Newburyport in the north, to Kingston Bay, just a few minutes away in Duxbury.

Running along quiet roads and linking conservation lands, and public parks, the trail is yet another way to appreciate Pembroke’s rural character.

If you’re up for a longer walk you can hike to the southern terminus at the Bay Farm Conservation Area in a few hours.

In Pembroke the trail passes through Pembroke Town Forest, Camp Wampatuck, and Tubbs Meadows, where it forks, with two paths through Duxbury that eventually meet at the trailhead.

Detailed static and interactive trail maps can be downloaded from the Bay Circuit Trail’s website and Pembroke’s town site.