Top 15 Attractions and Activities in Southborough, MA

Southborough is a residential town located in the MetroWest region, characterized by its historic center and a series of charming villages. Incorporated in 1727, it flourished as a manufacturing hub until the late 19th century, when the construction of the extensive Sudbury Reservoir submerged a significant area of the town.

This reservoir continues to serve as Boston’s backup water supply, and a five-mile trail weaves through Southborough, tracing the shore and the Wachusett Aqueduct that feeds into it. Outdoor enthusiasts will find ample opportunities for recreation in Southborough, highlighted by its proximity to two state parks and pastoral conservation lands interconnected by the 33-mile Boroughs Loop Trail.

1. Southborough Center Historic District

With origins dating back roughly 300 years, Southborough features an exceptionally picturesque village center, recently recognized on the National Register of Historic Places in 2021.

A notable highlight and landmark at the top of the hill is the distinguished Southborough Town House, built in the Italianate style in 1870.

The same architect, Alexander Esty, also designed the Gothic Revival St Mark’s Episcopal Church (1863). Beside the Town House, one can visit the Pilgrim Church (1806), which originally served as the Unitarian Church and was converted by the Pilgrim Congregational Church in 1857.

The small common is marked by a Veterans Memorial from 1866 and surrounded by a row of beautiful homes dating from the 18th and 19th centuries.

2. Sudbury Reservoir Trail

The central feature of Southborough’s landscape is the 5,000-acre Sudbury Reservoir, excavated in the 1890s.

Still utilized as an emergency backup for Boston’s water supply, the reservoir is integral to an interconnected system along the Sudbury River.

Water flows into the reservoir from the west via the Wachusett Aqueduct and is then directed through the Western Aqueduct to the Weston Reservoir further east.

Beginning at the causeway along Framingham Road, one can traverse five miles of the reservoir’s banks and follow the Wachusett Aqueduct in Southborough, moving westward to the border with Westborough.

Historical markers denote landmarks such as the Burnett House (1849), and a stunning wooded stretch exists between White Bagley Rd and Cordaville Rd.

Since the reservoir remains operational, dogs are not permitted, but numerous designated fishing spots are available along the trail.

3. Boroughs Loop Trail

The hiking pathways in Southborough, Westborough, Northborough, and Marlborough are gradually being connected to establish a 33-mile loop.

This impressive route utilizes sidewalks, bike paths, woodland cart paths, and aqueduct trails, providing an exceptional opportunity to explore the natural beauty surrounding these towns.

In Southborough, this trail includes a significant segment of the Sudbury Reservoir Trail and traverses paths at Chestnut Hill Farm and the Beals Preserve.

In the northwest part of Southborough, a scenic segment leads into the Cedar Hill and Sawink Farm preserve, managed by the Sudbury Valley Trustees.

4. Chestnut Hill Farm

Located approximately one mile west of Southborough Center, this working farm is one of the last of its kind in Southborough.

This picturesque expanse of pastures and upland forest, traced by historic stone walls, has been preserved due to efforts by a local family in the 1960s, in addition to community support that led to the establishment of a Conservation Restriction in 2006.

A cart path meanders past fields growing vegetables, alfalfa, and hay, rising into a forest of white pine, red maple, and oak. Chestnut Hill Farm operates a CSA program and features a seasonal farmstand offering homegrown produce.

5. Beals Preserve

A local couple generously donated this beautiful 55-acre parcel of land adjacent to the open channel of the Wachusett Aqueduct.

Managed by the Southborough Open Land Foundation, Beals Preserve boasts a network of trails that traverse woods, meadows, alongside a pond, and across the aqueduct.

The trails connect with the Sudbury Reservoir Trail and the Boroughs Loop Trail. The summer months are the best time to visit, as the preserve hosts the Art on the Trails event, showcasing engaging installations that transform the landscape into a sculpture garden.

6. Breakneck Hill Conservation Area

This 90-acre expanse of rolling land is owned by the town and accessible to the public for passive recreation.

During summer, Breakneck Hill delights visitors with meadows adorned with wildflowers. On a clear day, views extend for miles.

Under the right conditions, you can even spot Mount Wachusett in the distance. The hilly terrain features some challenging climbs, and there is a 1.4-mile loop trail that begins at the parking area located in the southwest corner of Breakneck Hill Road.

7. Callahan State Park

A small section of the 950-acre Callahan State Park extends into Southborough’s northeastern corner. Primarily situated in Framingham and Marlborough, the park was opened to the public in 1970 and features inviting stretches of woodland and open fields, surrounding Beebe Pond and Eagle Pond.

Callahan State Park is also an attraction on the Bay Circuit Trail, offering seven miles of marked trails suitable for hiking, horseback riding, mountain biking, and cross-country skiing when snow covers the ground.

The area surrounding Eagle Pond is an unofficial dog park, frequently visited by pet owners seeking to exercise their dogs off-leash.

8. Eastleigh Farm

Originating from the early 20th century, this historic farm was acquired by its current owner to prevent redevelopment.

Over the past 20 years, Eastleigh Farm has reverted to its origins as a dairy farm while also inviting the public for seasonal events.

On a typical day, the chief attraction is the homemade ice cream, produced on-site. Flavors such as Black Raspberry, Cookie Monster, Maple Walnut, and Chocolate Peanut Butter are delightful options.

Visitors can take a leisurely walk around the estate or enjoy a wagon ride to observe the cattle herd. On weekends, a multi-vendor vintage store and an antique shop can be accessed within a barn.

9. Trombetta’s Farm

This ice cream stand in nearby Marlborough is located near the northern tip of the Sudbury Reservoir.

Established in 1978, Trombetta’s Farm is one of the few ice cream shops that remain open throughout the year, albeit with reduced hours during the winter months.

With a selection of 40 flavors of homemade, traditional ice cream available, produced daily for optimal creamy texture and flavor, there are also options for sherbets, soft serve, sorbets, sugar-free flavors, and frozen yogurt.

A converted 450-foot greenhouse houses an 18-hole golf course on the premises.

The garden center predates the ice cream business and features a variety of annuals, perennials, succulents, and various gardening ornaments and accessories.

10. Southborough Golf Club

Featuring an affordable 9-hole course accessible to the public at all times, Southborough Golf Club is situated beside the Sudbury Reservoir, with the trail bordering the course.

The holes are arranged across rolling terrain with glacial erratics dispersed within the woods, offering views toward the Southborough Rural Cemetery, established in the mid-19th century.

The course has undergone renovations in recent years, improving all cart paths, tees, and bunkers.

11. Hopkinton State Park

The primary parking area for this popular state park is conveniently located near the Southborough rail station, just over the border in Hopkinton.

Founded in 1947, the main attraction of Hopkinton State Park is its inactive, spring-fed reservoir, which formerly served as part of Boston’s water supply.

Visitors can enjoy two swimming beaches along the shore, and during the season, kayak, canoe, and paddleboard rentals are available through Boating in Boston, which also offers sailing courses.

Numerous picnic areas with grills are available around the shoreline for family gatherings, while the adjacent woods and wetlands can be explored through an intricate network of trails.

12. Bay Circuit Trail

A recently completed segment of connecting trail by the Sudbury Reservoir to the east of Southborough is part of an expansive 230-mile route traversing Boston’s outer suburbs.

This trail, spanning from Newburyport in the north to Duxbury in the south, utilizes existing infrastructures and properties, which include sidewalks on quiet roads, conservation lands, trails, and public parks.

In Southborough, travelers can utilize this trail to explore a vast network of interconnected natural areas in Framingham and Sudbury.

Following the Sudbury Reservoir Trail leads into Callahan State Park, from which visitors can proceed to Henry’s Hill and Wayside Forest, managed by the Sudbury Valley Trustees.

13. Southborough Golf-Learning Center

This driving range, situated off Route 9, offers another opportunity to refine your golf skills. One notable advantage of the Southborough Golf-Learning Center is its scenic location on a wooded hillside, providing a natural backdrop for practice.

The range features floodlighting and provides a choice between grass and artificial tees. Additionally, heated bays allow for practice during winter months.

Several golf professionals at the center offer private and group lessons that include video analysis, and a full-service club repair shop is also available.

14. Fayville Park

Located in Southborough’s Fayville village, this well-equipped public park is set on a slope overlooking the reservoir.

Fayville Park is particularly favorable for families, boasting a remarkable playground with distinct climbing structures and swings designated for children aged 1-5 and 5-12.

Just a short distance away, a shaded picnic shelter provides ample seating and clear views of both the playground and the reservoir. Additionally, Fayville Park includes a single-hoop basketball court and a baseball/softball diamond.

15. Heritage Day

For over fifty years, Southborough has celebrated the fall season in October with a large annual gathering.

Primarily hosted at St. Mark’s Field, located at the intersection of Routes 85 and 30, Heritage Day offers a rich array of activities within a few hours.

The event features a parade, numerous food and craft vendors, free demonstrations by local organizations and businesses, and various engaging attractions and activities suitable for children.

Participants in the parade include veterans, local fire and police departments, school marching bands, scouts, and youth sports teams.