This body of water is still part of Boston’s backup water supply, and there’s a five-mile trail through Southborough tracing the shore and the Wachusett Aqueduct that feeds it. There’s no shortage of inspiration for outdoor recreation in Southborough, with two state parks nearby, and pastoral conservation lands connected by the likes of the 33-mile Boroughs Loop Trail.

1. Southborough Center Historic District

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Dating back some 300 years, Southborough has an exceedingly quaint village center, added to the National Register of Historic Places as recently as 2021.

The crowning glory and landmark at the top of the slope is the fine Southborough Town House, constructed in the Italianate style in 1870.

The same architect, Alexander Esty, designed the Gothic Revival St Mark’s Episcopal Church (1863). On the other side of the Town House stands the Pilgrim Church (1806).

Originally the Unitarian Church, this is on the site of Southborough’s first meetinghouse, and in 1857 was purchased by the breakaway Pilgrim Congregational Church.

Down the slope the little common is centered on a Veterans Memorial from 1866, and edged by a row of elegant houses from the 18th and 19th century.

2. Sudbury Reservoir Trail

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The dominant feature of Southborough’s townscape is the 5,000-acre Sudbury Reservoir, which was excavated in the 1890s.

Still active as an emergency backup water supply for Boston, the reservoir is part of an interlinked system along the Sudbury River.

Water was delivered into the reservoir from the west via the Wachusett Aqueduct, and then sent along the Western Aqueduct to the Weston Reservoir several miles to the east.

Starting by the causeway along Framingham Road, you can follow five miles of the reservoir’s shores and the Wachusett Aqueduct in Southborough, heading west as far as the line with Westborough.

Historical markers point out landmarks like the Burnett House (1849), while there’s a gorgeous wooded stretch between White Bagley Rd and Cordaville Rd.

As the reservoir is still active, no dogs are allowed, but there are plenty of designated fishing spots on the trail.

3. Boroughs Loop Trail

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The hiking networks in Southborough, Westborough, Northborough and Marlborough are in the process of being linked up to create a 33-mile loop.

Using sidewalks, bike paths, woodland cart paths, and aqueduct trails, this is a fantastic way to appreciate the abundance of natural beauty in these towns’ backyards.

In Southborough the trail incorporates a big section of the Sudbury Reservoir Trail, as well as paths at Chestnut Hill Farm and the Beals Preserve.

Starting in the northwest of Southborough, there’s also a beautiful section taking you into the Cedar Hill and Sawink Farm preserve, in the care of the Sudbury Valley Trustees.

4. Chestnut Hill Farm

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About a mile west of Southborough Center there’s a working farm, one of the last of its kind in Southborough.

This beautiful tract of pastures, upland forest, all traced by old stone walls, has been preserved thanks to the efforts of a local family in the 1960s, as well as the citizens of Southborough who voted to purchase a Conservation Restriction here in 2006.

A cart path skirts past fields growing vegetables, alfalfa and hay, and climbs into a forest of white pine, red maple and oak. Chestnut Hill Farm runs a CSA program, but also has a seasonal farmstand selling homegrown produce.

5. Beals Preserve

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A local couple donated this lovely 55-acre tract of land sitting by the open channel of the Wachusett Aqueduct.

Beals Preserve is managed by the Southborough Open Land Foundation, and has a web of trails in woods, over meadows, next to a pond and across the aqueduct.

The trails here connect with the Sudbury Reservoir Trail and with it the Boroughs Loop Trail. The best time to be here is in the summer, when the preserve hosts the Art on the Trails event, with engaging installations turning the landscape into a sculpture park.

6. Breakneck Hill Conservation Area

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

Breakneck Hill is a joy in summer when the meadows are scattered with wildflowers. Come on a clear day and the views reach out for miles.

You can even see as far as Mount Wachusett if the conditions are right. The hilly topography presents some stiff climbs, and there’s a 1.4-mile looping trail beginning at the parking lot in the southwest corner of the reservation on Breakneck Hill Road.

7. Callahan State Park

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A small piece of the 950-acre Callahan State Park is on Southborough’s northeastern nook. Mostly in Framingham and Marlborough, the park opened to the public in 1970, with inviting expenses of woodlands and open fields, surrounding Beebe Pond and Eagle Pond.

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

The area around Eagle Pond in the southernmost section is an unofficial dog park, as a favored place to exercise pups off leash.

8. Eastleigh Farm

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Dating back to the turn of the 20th century, this historic farm was purchased by its current owner to avoid it being redeveloped.

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

On an average day, the main reason to visit is for the ice cream, which is made on site. Black Raspberry, Cookie Monster, Maple Walnut and Chocolate Peanut Butter are a few of the great flavors.

You can also take a leisurely walk around the property, or book a wagon ride to see the cattle herd. On weekends you can call in at a multi-vendor vintage store, as well as an antique dealer, housed in a barn.

9. Trombetta’s Farm

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This ice cream stand in nearby Marlborough is situated close to the northern tip of the Sudbury Reservoir.

Going back to 1978, Trombetta’s Farm is one of those rare ice cream shops that stays open all year, with reduced hours (weekends) in the winter months.

There are 40 flavors of homemade, old-fashioned ice cream to choose from. These are made daily to ensure a creamy texture and taste, and there’s also a choice of sherbets, soft serve, sorbets, sugar-free flavors and frozen yogurt.

Trombetta’s Farm has an 18-hole golf course on the property, housed in a converted 450-foot greenhouse.

The garden center here predates the ice cream operation, and offers an abundance of annuals, perennials, succulents, houseplants, hanging plants, garden ornaments and accessories.

10. Southborough Golf Club

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This reasonably priced 9-hole course is open to the public at all times. Southborough Golf Club is in an attractive spot, bounded to the south by the Sudbury Reservoir, with the trail skirting the edge of the course.

The holes are laid out on undulating terrain, with glacial erratics hiding in the woods and views east to the Southborough Rural Cemetery, dating back to the mid-19th century.

The whole course has undergone an update in the last few years, renovating all of the cart paths, tees, and bunkers.

11. Hopkinton State Park

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The main parking lot for this popular state park is a stone’s throw from Southborough rail station, just over the line in Hopkinton.

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

There are two swimming beaches on the shore, and during the season you can rent kayaks, canoes, and paddleboards courtesy of Boating in Boston, which also offers sailing courses here.

You’ll find multiple picnic areas with grills around the shoreline where you can enjoy a family cookout, while the surrounding woods and wetlands can be discovered on a tangle of trails.

12. Bay Circuit Trail

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A stretch of newly completed connecting trail, by the Sudbury Reservoir in the east of Southborough is part of an epic, 230-mile trail weaving through Boston’s outer suburbs.

On its journey from Newburyport in the north to Duxbury in the south, the Bay Circuit Trail uses existing infrastructure and properties, from sidewalks on quiet roads to conservation lands, trails and public parks.

In Southborough you could use the trail to visit an enormous sequence of interconnected natural spaces in Framingham and Sudbury.

After the Sudbury Reservoir Trail you’ll enter Callahan State Park, and from there you’ll move onto Henry’s Hill and Wayside Forest, maintained by the Sudbury Valley Trustees.

13. Southborough Golf-Learning Center

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Another place to fine-tune your golf game is this driving range off Route 9. Something going for the Southborough Golf-Learning Center is the location, as the range is draped over a wooded hillside with nothing but trees bordering targets.

The range is floodlit, and there’s a choice between grass and artificial tees. You can work on your swing in the winter thanks to a set of heated bays.

There are a couple of pros based at the center offering private and group lessons, with video analysis, and you’ve also got a full-service club repair business here.

14. Fayville Park

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In Southborough’s Fayville village there’s a well-equipped public park, laid out on the slope overlooking the reservoir.

Fayville Park shines most of all as a place to bring children. There’s a fantastic playground here, with separate climbing structures and swings for kids aged 1-5 and 5-12.

A few steps away there’s a picnic shelter with plentiful shade and clear lines of sight of both the playground and the reservoir. Fayville Park also has a single-hoop basketball court, and a baseball/softball diamond.

15. Heritage Day

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For half a century now, Southborough has marked the fall season in October with a big annual get together.

Mostly anchored by St. Mark’s Field, at the corner of Routes 85 and 30, Heritage Day packs a lot into just a few hours.

For a brief summary, there’s a parade, dozens of food and craft vendors, free demonstrations by local clubs and businesses, and a host of child-friendly attractions and activities.

Some of the groups and services taking part in the parade include veterans, the fire department, police, school marching bands, scouts and youth sports teams.

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