In southeastern Massachusetts, the town of Middleborough is wrapped in lovely rural landscapes of mill brooks, cranberry bogs and the largest lakes in the state.
The old center of town hasn’t changed much in more than a century, with a stately town hall and library building, and grand commercial architecture going back deep into the 19th century.
The Nemasket River flows through Middleborough on its way to Assawompset Pond, and is the route of a huge fish migration in spring, when hundreds of thousands of alewife and blueback herring head upstream to their spawning grounds.
Fish ladders have been installed to help the herring on their way, and there are a couple of places where you can watch this natural spectacle in late March and early April.
1. Middleborough Center
The historic center of Middleborough was developed between the mid-1800s and the 1920s, and has kept much of its architecture from that period.
The Historic District here covers 220 acres and includes more than 500 buildings, with grand civic landmarks like the Victorian-style Town Hall (1870s), and important examples of commercial architecture like the Peter Pierce Store (1825), which until recently served as the town’s police headquarters.
Main Street and the snaking Center Street have a lot to hold your interest, with a gallery, museums, a performing arts venue, a clutch of eateries and one of the top antique centers for miles.
2. The Oliver Estate
One figure prominent in 18th-century Middleborough was the Loyalist Peter Oliver (1713-1791), who served as Chief Justice of the Superior Court of the Province of Massachusetts Bay in the early 1770s.
Oliver was a successful businessman and set up an ironworks here in the 1740s, the remnants of which can be seen on the Nemasket River.
Oliver’s estate is slightly to the north, and centers on an elegant Georgian house from 1769. The grounds are open Monday to Friday all year round, while the house normally opens for seasonal special events, as well as an annual schedule of guided tours, June through September.
Over the years, the Oliver House has gained the attention of ghost hunters, and there are spooky tours each year around Halloween.
3. Middleborough Historical Museum
Operated by volunteers, the Middleborough Historical Museum is on a campus of seven buildings in the town center, and is normally open June through October.
The museum is known for having one of the largest collections relating to the famous circus performer, Charles Sherwood Stratton (General Tom Thumb) (1838-1883), who became a star under P. T. Barnum.
Lavinia Warren (1841-1919), Stratton’s wife, hailed from Middleborough. She was a famous personality in her own right, remarrying and running a roadside stand in her hometown after his death.
The Tom Thumb Collection is in the main building, a Mill House from 1820. Other structures include the Judge Wood Law Office (1794), the Whistle House (c. 1800s), and reproductions of a carriage house, blacksmith shop and five-seat outhouse.
4. Oliver Mill Park
Along the Nemasket River on the south side of Route 44 you can explore the remnants of the early industrial complex developed by Peter Oliver.
The history of the ironworks goes back to the 1730s, and Oliver took over in 1744, overseeing a significant enlargement, with workers flocking to what became one of the largest villages in the area.
Cannons, cannonballs, shovels and an array of household implements were produced at this very site up to its abandonment 1843.
There’s now a captivating archeological park here, with footbridges helping you view the masses of stonework lining the banks.
There’s a fish ladder here, and in early spring, Oliver Mill Park is one of several places where you can watch the alewife and blueback herring battling upstream towards Assawompset Pond.
5. Assawompset Pond Complex
At nearly four square miles, Assawompset Pond in the southwest of Middleborough is the largest natural lake in Massachusetts.
On a site important for the Wampanoag Tribe, this drinking water reservoir is part of a vast complex made up of five other lakes, couched in oak and evergreen forest and wooded swamp on a patchwork of protected lands.
As this is an active reservoir, water-based recreation is restricted to Long Pond in nearby Lakeville and Freetown. Betty’s Neck, on the southern shore of Assawompset Pond, is a favorite place for hikes, and you can see farmers harvesting cranberries in fall.
The causeway here between Pocksha and Great Quittacas ponds is home to the Between the Lakes scenic viewpoint, for dreamy sunrises and sunsets, as well as fantastic stargazing.
6. Robbins Museum of Archaeology
The Massachusetts Archaeological Society opened this museum in downtown Middleborough in 1988 and named it for Maurice “Doc” Robbins, the first State Archaeologist of Massachusetts.
The society’s collections are massive, numbering around 150,000 artifacts. The Robbins Museum goes into particular depth on Paleo-Indian archaeology, with extensive displays of tools, weapons and crafts discovered throughout New England.
You can view a mishoon (dugout canoe), and get a sense of life in Native American village some 4,300 years ago.
7. Edaville Family Theme Park
A matter of minutes away in Carver there’s a heritage railroad and amusement park that first opened to the public on a cranberry farm in 1947.
This makes Edaville one of the oldest operating heritage railroads in the country, with narrow gauge (two-foot) trains running on 2.5 miles of track. On your journey you can admire an idyllic, watery landscape of cranberry bogs as the train passes along the levees.
The cars are often pulled by Thomas the Train, who also has an entire zone at the park, called Thomas Land, with 11 rides designed for younger children.
Dino-Land meanwhile is inhabited by more than 23 lifesize animatronic dinosaurs, while the theme park’s main area has upwards of 30 rides, many based loosely on the railroading and cranberry themes.
8. Soule Homestead Education Center
For more than 30 years this town-owned farm has been open to the public for free. On 120 acres, the Soule Homestead Education Center is open every day of the year, from sunrise to sunset, and is the setting for numerous programs, activities and events in every season.
If you’re around in summer there’s a sheep shearing day, an annual summer concert series, and a harvest fair late in the season.
On a typical day you could also just stop by to explore the extensive nature trails, and bring children to see the horses, goats, cows, sheep, chickens and rabbits.
9. Rocky Gutter Wildlife Management Area
There’s a remote state-owned refuge in the south of Middleborough covering 3,000 acres, ideal for walking, mountain biking, trail running and photography.
You can make your way through large stands of mature pine and oak, and past white cedar swamps via more than 15 miles of old logging trails.
These trails are wide and level, but aren’t marked so you’ll need to bring or download a map, and be comfortable using a compass.
For mountain bikers, this is one of those rare spots without hills, perfect for beginners, kids or anyone in search of lighter terrain. As this is a wildlife management area, it’s worth checking the hunting season schedule before coming.
10. Middleborough Public Library
A sight to behold downtown is the Middleborough Public Library, built in the Beaux-Arts style in 1903. As an institution, the library dates back to 1874, and started out as a room in the Town Hall.
Constantly moving with the times, this is a fantastic asset for the community, brimming with programs for all ages.
The library is also part of the SAILS Network of 70 libraries in the southeast of Massachusetts, as well as a statewide virtual catalog.
If you’re only in town for a short time, the kids’ room is an inspiring place to bring children for an hour or two, while there’s a range of services that you can use with a guest pass, like the public computers.
11. Wareham Street Herring Run (Thomas Memorial Park)
Assawompset Pond is a spawning ground for many hundreds of thousands of alewife and blueback herring, and you can come to this fish ladder on the Nemasket River, close to Middleborough Center to see them making their journey upstream.
The annual alewife herring run, one of the largest on the Eastern Seaboard, takes place between mid-March and early April.
The name “Nemasket”, is thought to mean “place where the fish are” in Wampanoag. Thomas Memorial Park here is also one of a few put in places along the river for paddlers.
12. The Alley Theatre
At 133 Center St, downtown Middleborough has a compact performing arts space, opened in 2010 by the Burt Wood School of Performing Arts.
This is a refined space for concerts, musicals, plays, drag shows, comedy sets, benefits, seminars, fairs, as well as private functions from birthday parties to bridal showers. There’s seating for 100 guests, on folding, thickly padded seats.
If you’re coming to Middleborough, keep an eye on the calendar for details of upcoming shows. In the summer there’s an outdoor concert series on the adjoining Patio at the Alley Theatre.
13. Benson’s Pond Farm
If you’ve ever wanted to see an active cranberry bog, there’s a third generation farm in South Middleborough, part of the Ocean Spray Cooperative. Benson’s Pond Farm is of course private, but does offer tours by appointment.
You’ll get a privileged glimpse of a form of agriculture unique to the southeast of Massachusetts, and the ideal time to come is in late fall, around harvest time when you can put on waders and become a “Cranberry Bogger for the Day”.
There are 40 acres of bogs here, bordered by upland areas and woods. The 1940s Barn at Benson’s Pond, in a picturesque location overlooking the bogs, is rented out for weddings.
14. Middleboro Antique Co-op
In the heart of downtown Middleborough, the Grant Building at 40 N Main St houses a multi-vendor antique cooperative. Over 20,000 square feet, there are more than 120 vendors here, and the mall seems to go on and on.
Allow as much time as you can afford to browse antique furniture, ceramics, signage, lighting, silver, old-time farming tools, toys, glassware, vinyl, license plates, home appliances, clocks, art, jewelry, fashion accessories, sports equipment, dolls, books, cookware and much more.
For a nice change from many antique centers, the Middleboro Antique Co-op has a very orderly feel and is dust-free.
15. Off the Wall Kidz
Next door in Carver there’s a location for an award-winning mini-chain of indoor playgrounds. Off the Wall Kidz has something for all ages, from toddlers up to 12.
The main attraction is a giant, custom-designed play structure with a maze of climbing structures, as well as trampolines, slides and bridges.
There’s an educational element to the Pretend City, where younger children will have fun roleplaying everyday situations, with streets, mini cars, a fire station and amenities like a supermarket and medical clinic.
Off the Wall Kidz also has an arcade, a designated toddler play area, a ball pit and an interactive slide.