15 Best Things to Do in Southborough (MA)

Comprising a historic center and a group of villages, Southborough is a residential city in the MetroWest region. Southborough was incorporated in 1727 and flourished as a commercial area until the late 19th century. That all changed in the 1890s when he found much of the city suddenly submerged after the construction of the enormous Sudbury Reservoir.

The waters are still part of Boston’s reserve aqueduct, with five miles of hiking trails along the Southborough coast and through the Wachusett Aqueduct that feeds it. Southborough has no shortage of inspiration for outdoor recreation. For example, his two nearby state parks and idyllic reserves are connected by his 53-mile Borrows Loop Trail.  

1. Hopkinton State Park

Hopkinton State Park

The main parking lot at this popular state park is just off the Hopkinton Line and a stone’s throw from Southborough Station.

Established in 1947, Hopkinton State Park’s main attraction is a now-inactive spring-fed reservoir formerly part of Boston’s water supply system.

There are two bathing beaches on the coast. During the season, kayaks, canoes, and paddleboards can be rented from Boston’s boat shop. Sailing lessons are also offered here.

There are several picnic areas with barbecue grills around the beach for family barbecues. You can also explore the surrounding forests and swamps along maze-like paths. 

2. Bay Circuit Trail

Bay Circuit Trail

Part of the newly completed Link Trail at Sudbury Reservoir in East Southborough is part of an epic 230-mile trail that winds through the Boston suburbs.

From Newburyport in the north to Duxbury in the south, the Bay Circuit Trail utilizes existing infrastructure and land, from quiet road trails to nature reserves, trails, and public parks.

In Southborough, this trail allows you to visit vast interconnected natural areas in Framingham and Sudbury.

After traversing the Sudbury Reservoir Trail, enter Callahan Provincial Park and from there to Henry’s Hill and Wayside Forest, managed by the Sudbury Valley Board of Trustees.  

3. Southborough Golf-Learning Center

Southborough Golf-Learning Center

Another place to hone your golf skills is this driving range along Route 9. A plus point of the Southborough Golf Learning Center is its location. The practice range is spread out on a lush hillside, with only trees surrounding the target.

The course is illuminated and you can choose between grass tees and artificial tees. There is a heated parking space so you can enjoy the swing even in winter.

The center has several specialists who offer private and group lessons using video analytics. We also have a full-service racket repair company. 

4. Fayville Park

Fayville Park

The village of Fayville in Southborough has a well-maintained public park on a hillside overlooking a reservoir.

Faville Park especially shines as a place for children. Here you’ll find a great playground with separate jungle gyms and swings for children ages 1-5 and 5-12.

A few steps away is a picnic area with plenty of shade and unobstructed views of the playground and reservoir. Faville Park also has a basketball court and a baseball/softball field. 

5. Heritage Day

Heritage Day

For half a century, Southborough has celebrated the fall season with a major gathering each October.

Heritage Day packs a lot into just a few hours, with its main venue being St. Marks Field at the intersection of Routes 85 and 30.

In summary, there are parades, dozens of food and craft stalls, free performances by local clubs and businesses, and a variety of attractions and activities for children.

Organizations and groups participating in the parade include veterans, firefighters, police, school marching bands, Boy Scouts, youth sports teams, and others. 

6. Breakneck Hill Conservation Area

Breakneck Hill Conservation Area

This 90-acre rolling vacant lot is owned by the city and is open to the public for passive recreation.

Breakneck Hill is perfect for summer when the meadows are dotted with wildflowers. Come on a clear day and you’ll have views for miles.

If the conditions are right, you can see all the way to Wachusett Mountain. The hilly terrain includes some steep climbs and a 2.4-mile loop trail that begins at the parking lot in the southwest corner of the reserve on Breakneck Hill Road.  

7. Callahan State Park

Callahan State Park

A small portion of the 950-acre Callahan State Park is located in the northeast corner of Southborough. Located primarily in Framingham and Marlborough, the park opened to the public in 1970 and included attractive woodlands and fields around Beeb and Eagle Ponds.

Another local attraction on the Bay Circuit Trail, Callahan State Park has 11 miles of marked trails for hiking, horseback riding, mountain biking, and after-snow cross-country skiing.

The southernmost Eagle Pond area is an unofficial dog run and a popular spot for off-leash puppies. 

8. Eastleigh Farm

Eastleigh Farm

This historic farm dates back to the beginning of this century and was purchased by the current owners to avoid redevelopment.

Over the last 20 years, Eastleigh Farm has returned to its roots as a dairy farm but has also been open to the public for seasonal events.

The main purpose of an average daily visit is the ice cream made on the spot. Black Raspberry, Cookie Monster, Maple Walnut, and Chocolate Peanut Butter are just a few of the great flavors.

Take a leisurely stroll around the grounds or book a covered wagon to see the herds of cattle. On weekends, you can stop by the multi-vendor vintage shops and barnyard antique dealers. 

9. Trombetta’s Farm

Trombetta’s Farm

Near Marlborough, this ice stand is near the northern end of Sudbury Reservoir.

Since 1978, Trombetta’s Farm is he one of the rare ice cream parlors that are open year-round, although with limited hours (weekends) during the winter months.

About 40 kinds of homemade ice cream. These are cooked daily to ensure a creamy texture and taste. There are also sherbets, soft serve ice cream, sherbets, sugar-free flavors, and frozen yogurt.

Trombetta’s Farm has an 18-hole golf course in a converted 450-foot-tall greenhouse. The garden center here predates ice cream parlors and offers a wide selection of annuals, perennials, succulents, houseplants, hanging plants, garden ornaments, and supplies. 

10. Southborough Golf Club

Southborough Golf Club

This affordable 9-hole course is always open to the public. Southborough Golf Club is attractively situated, surrounded by Sudbury Reservoir to the south, with paths circling the system.

The hole is located in a hilly area, a glacier fault hidden in the forest, and offers an eastern view of the mid-19th-century Southborough Regional Cemetery.

The entire course has been modernized in recent years with all kart tracks, tees, and bunkers refurbished. 

11. Southborough Center Historic District

Southborough Center Historic District

Southborough is nearly 300 years old, has a very beautiful village center, and was just added to the National Register of Historic Places in 2021.

The crowning glory and landmark at the top of the hill is the beautiful Southborough Town House, built in 1870 in Italian style.

The same architect Alexander His Estee designed his Neo-Gothic St. Mark’s Episcopal Church (1863). Opposite the Town Hall is the Pilgrimage Church (1806).

Originally on the site of Southborough’s first meetinghouse, the Unitarian church was purchased by the detached Pilgrim Congregational Church in 1857. The small hillside community is centered around the 1866 Veterans Memorial and is lined with elegant 18th- and 19th-century homes. 

12. Sudbury Reservoir Trail

Sudbury Reservoir Trail

A major feature of the Southborough cityscape is the 5,000-acre Sudbury Reservoir, excavated in the 1890s.

The reservoir still serves as Boston’s emergency water supply and is part of the interconnection system along the Sudbury River.

Water entered the reservoir from the west through the Wachusett Aqueduct and then along the West Aqueduct to Weston Reservoir several miles east.

Starting on the causeway along Framingham Road, you can follow the 8-mile coastline of Southborough Reservoir and Wachusett Aqueduct westward to the Westboro border.

Historic markers point to landmarks such as Barnett House (1849), and beautiful woodland stretches between White-Bagley Road and Caudaville Road.

The reservoir is still active, so dogs are not allowed, but there are many designated fishing spots along the way. 

13. Boroughs Loop Trail

The Southborough, Westborough, Northborough, and Marlborough walking networks are now consolidated into 53 miles of circular trails.

Footpaths, bike paths, forest cart paths, and aqueduct paths are great ways to enjoy the abundant natural beauty of these urban backyards.

Southboro’s trails include most of the Sudbury Reservoir Trail, as well as those of Chestnut Hill Farm and Beale’s Preserve.

There is also a beautiful section that starts northwest of Southborough and heads to Cedar Hill and Soink Farm Reserve, managed by the Sudbury Valley Trustees.  

14. Chestnut Hill Farm

Chestnut Hill Farm

About a mile west of the Southborough Center is one of the last farms in Southborough, a working farm.

Surrounded by ancient stone walls, this beautiful rangeland and highland woodland was saved thanks to the efforts of local families in the 1960s and Southborough citizens who voted to purchase a conservation limit in 2006.

The wagon road winds through fields of vegetables, alfalfa, and hay and climbs into forests of white pine, red maple, and oak. Chestnut Hill Farm runs its CSA program but also has a seasonal farmer’s booth selling homegrown produce.  

15. Beals Preserve

Beals Preserve

A local couple donated this beautiful 55-acre property on the open canal of the Wachusett Aqueduct.

Managed by the Southborough Open Land Foundation, Beal’s Reserve features a network of trails across woodlands, meadows, ponds, and aqueducts.

Trails here lead to the Sudbury Reservoir Trail and the Borrows Loop Trail. The best time to visit is in the summer when the nature reserve hosts Art on the Trail events, where fascinating installations transform the landscape into a sculpture park.  

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