Top 15 Attractions and Activities in Westborough, MA

Established in 1717, Westborough is a rapidly developing town with a population of approximately 22,000, situated less than ten miles east of Worcester.

Westborough presents an upscale ambiance, evident in the elegant historic commercial buildings downtown, as well as the grand residences along West Main Street and its adjoining streets.

Abundant town-owned green spaces enhance the community, with numerous areas connected through the Charm Bracelet Trail System, which offers nearly 30 miles of continuous trails winding throughout the town.

During the summer months, Westborough’s community spirit is palpable at events such as the July 4th Block Party, along with various family-oriented entertainment options hosted on Bay State Green.

1. Downtown Westborough

Where Main Street, South Street, and Milk Street converge, Westborough boasts a charming central commercial district, harmonizing history, dining, and an active events calendar.

Main Street features numerous examples of intricate commercial architecture from the 19th century, including the Arcade Building (1890), the American Block (1871), and the Spaulding Block (1872).

West Main Street hosts a historic district that preserves splendid homes and landmarks such as the Westborough Public Library (1908) and the Evangelical Congregational Church (1834).

In the vicinity of the downtown roundabout, various eateries offer diverse cuisines including Korean, Thai, Japanese, BBQ, pub fare, pizza, and classic American diner selections.

2. The Sibley House (Westborough Historical Society)

One of the elegant homes on Parkman Street, just off West Main Street downtown, serves as the headquarters of the Westborough Historical Society, established in 1889.

This is the Sibley House (No. 13), constructed by successful blacksmith and wheelwright William Sibley in 1844. Characterized by the dominant Greek Revival style, Sibley operated a wagon shop in an outbuilding on the premises.

Sibley served in the Civil War and sustained injuries at the Battle of Antietam in 1862, subsequently returning to become a prosperous sleigh maker in Westborough.

The historical society acquired the Sibley House in 1990, which now houses an extensive collection of decorative arts along with exhibits detailing over 300 years of local history.

3. Westborough Charm Bracelet Trail System

The town features a significant amount of public open space designated as conservation areas, and since 2000, efforts have been made to connect most of these areas via a 28-mile trail loop.

As of the current year, much of the Westborough Charm Bracelet Trail System is complete, allowing for extensive exploration of the town through forest, cedar swamp, and lakeside pathways.

Lake Chauncy is particularly picturesque, serving as the location of the Town Beach in summer, which is accessible only to residents of Westborough and Northborough.

Rich historical elements are found along the trails, including some of the town’s earliest roads, a segment of the Boston and Worcester Street Railway (1903), centuries-old burial sites at Pine Grove and St. Luke’s Cemeteries, and Paleo-Indian sites at the Cedar Swamp Archeological District.

4. Cold Harbor Brewing

Located less than half a mile from downtown Westborough on Milk Street is a small-batch brewery that sources many of its ingredients from partner farms in the region.

Cold Harbor Brewing offers a diverse array of beers, with a particular focus on citrusy New England IPAs, featuring five varieties on tap during our last visit.

Additionally, the brewery typically features a stout (Milk Mustache), golden ale (Truell’s Gold), brown ale (Jackson Brown), and a Kölsch (Last Light).

Food trucks from the area frequently serve a variety of beer-compatible dishes such as Indonesian street food, BBQ, hot dogs, brick oven pizza, and burritos.

5. Harry’s Restaurant

Located on Route 9 in Westborough, this classic American diner has been family-owned and operated for nearly 80 years.

The extensive menu features homestyle dishes ranging from salads and pastas to burgers, sandwiches, shepherd’s pie, fried chicken, and ribs.

Specializing in New England-style seafood, options include lobster rolls, lobster bisque, scallops, fish and chips (haddock), and fried clams, among many others.

For a sample, the Harry’s Great Combo provides a delightful maritime platter of haddock, clam bellies, scallops, shrimp & calamari, served with french fries, coleslaw, and onion rings.

A favorite non-seafood option is the macaroni & cheese, presented with a homemade cheese sauce and cracker crumbs, appealing to both children and adults.

6. Crane Swamp

Adjacent to Lake Chauncy, the Westborough Charm Bracelet Trail System traverses a large expanse of cedar swampland within a 427-acre property.

Beyond the ecologically diverse swamp habitat, the path invites exploration through open fields, oak forest, and scenic wet meadows.

While enjoying nature, keep an eye out for river otters and a resident pack of coyotes playing in the fields. Note that hunting is permitted year-round (excluding Sundays) in this area, so walkers are advised to wear orange for safety.

7. Whitehall State Park

Accessible from Route 135, the Whitehall Reservoir can be reached within minutes from downtown Westborough.

This 620-acre Great Pond offers a secluded atmosphere, situated within an 837-acre state recreation area designated in 1947 after the reservoir ceased operations as a water source.

A hiking path encircles the entire shore, measuring approximately 8.5 miles, providing ample time to complete at a comfortable pace.

This area is ideal for kayaking, with small islands in the center accessible only by water. The fishing opportunities are abundant, particularly for trout and largemouth bass.

8. Bay State Green

Situated along Union Street in Downtown Westborough, this appealing green space features paved paths, newly planted trees, seating areas, a small playground, and a bandstand.

Bay State Green serves as the preferred location for summer events and festivals, including the July 4th Block Party.

One notable event is the popular summer concert series, featuring family-friendly performances every Tuesday evening in July and August.

Additionally, Screen on the Green provides outdoor movie screenings during July, complemented by local businesses like Uhlman’s Ice Cream and the BORO Sugar Shack, which offer delicious treats. Attendees are encouraged to bring lawn chairs or blankets for comfort.

9. Broken Creek Vineyard and Winery

Spanning 40 acres, this family-owned vineyard and winery is situated in the Shrewsbury countryside, approximately ten minutes from downtown Westborough.

Originally planted in 2011, the vineyard has expanded throughout the 2010s, with an old barn converted into the winery, which opened in 2015.

Visitors can enjoy a selection of wines produced from estate-grown varietals such as Cayuga White, Vignoles, Vidal Blanc, Traminette, and Marquette grapes, in addition to grapes sourced from growers in California.

A wine tasting option is available to sample a variety of selections, or opt for a flight of four 2 oz. pours. Autumn is an excellent time to visit, allowing participation in the harvest and observing a skilled winemaker in the process of destemming and crushing grapes.

10. Chestnut Hill Farm

The Trustees of Reservations oversee one of the last functioning farms in the neighboring town of Southborough, near the border with Westborough, in a truly picturesque setting with 170 acres of oak, maple, and pine forests, rolling fields, and pastures framed by historic stone walls.

Cart paths meander through a rich tapestry of habitats, transitioning from wooded hillsides to the edges of freshwater wetlands.

The farm operates a certified-organic CSA program; for those just passing by, the farmstand offers Trustees-grown products including meat, produce, and eggs, alongside high-quality honey, preserves, dairy products, sauces, and more sourced from local producers.

11. Westborough Golf Club

Founded in 1921 on a hilly landscape, Westborough’s municipal 9-hole course has earned a notable reputation, featuring quick greens and stunning views from its elevated tees.

With four sets of tees available, the course caters to golfers of various skill levels, whether playing nine or eighteen holes.

The standout holes include the spectacular third hole, a dogleg par 5 with an elevated tee, and the seventh hole, which is a sharp downhill par 3 offering views across Westborough.

12. Uhlman’s Ice Cream

This well-known ice cream stand in Westborough is managed by a family with a long-standing tradition in ice cream production dating back to 1940.

Founded as a farm stand in 1967, Uhlman’s Ice Cream soon dedicated itself to ice cream and is currently in its third generation of ownership.

The location is particularly charming, with dairy cows grazing in the adjacent fields.

With more than 70 hard ice cream flavors available, as well as frozen yogurt, allergy-friendly, and no added sugar options, the selections are complemented by a wide variety of toppings, from whipped cream to cookie dough.

Signature flavors include the tangy yet creamy Black Raspberry, which features several delightful variations, including Oreo pieces, dark chocolate chips, and both white and dark chocolate chunks (Purple Cow).

13. George H. Nichols Reservoir

Encompassed within the Westborough Charm Bracelet Trail System, the George H. Nichols Reservoir spans 313 acres and was acquired by the state in the 1960s for flood control purposes.

A collection of town-owned properties facilitates the Charm Bracelet’s connection to a chain of trails that follows the shoreline, extending from Mill Pond School in the south, through Veterans Freedom Park in the east, and past the Westborough train station in the north.

A trail parking lot is available at the station on the north shore, and all trails around the reservoir feature gentle grades, rendering them suitable for winter cross-country skiing, and showcasing a splendid array of wildflowers in the summer.

14. FORE! Golf Entertainment

Across from the Westborough Shopping Center on the Boston-Worcester Turnpike, an innovative golfing experience awaits.

FORE! Golf Entertainment features state-of-the-art simulators that allow players to navigate dozens of the world’s most iconic golf courses, from The Old Course at St Andrews to Pebble Beach Golf Links.

In addition to offering golf enthusiasts the opportunity to experience their dream courses, it serves as a perfect venue to maintain skills during the Massachusetts winter, complemented by an array of scenic driving ranges.

Furthermore, FORE! Golf Entertainment operates as a high-quality sports bar, complete with HDTV screens, comforting pub fare, and an extensive wine and beer selection.

15. July 4th Block Party

Typically occurring on the Friday before Independence Day, the July 4th Block Party is a cherished community gathering downtown.

Vendors line Main Street, providing diverse offerings, while live performances and activities take place on Bay State Green.

Recent celebrations have presented an array of food choices from local enterprises and chains, alongside entertaining activities for children, including a dunk tank, hay and pony rides, inflatables, and face painting.

A longstanding highlight is a performance by The Reminisants, a local oldies cover band active since 1973.