15 Best Things to Do in Westborough (MA)

Incorporated in 1717, Westborough is a fast-growing town of 22,000, less than ten miles east of Worcester.

Westborough has an upmarket air, reflected in the stately old commercial blocks downtown, and the palatial houses along West Main Street and its intersecting streets.

There’s no shortage of town-owned green space, and the many parcels have slowly been knitted together by the Charm Bracelet Trail System, snaking around the town with almost 30 miles of continuous trails.

Come in summer, and Westborough’s sense of community is unmistakable at events like the July 4th Block Party, and many evenings of family-oriented entertainment on Bay State Green.

1. Downtown Westborough

At the point where Main Street, South Street and Milk Street all meet, Westborough has a lovable central commercial district, blending history, dining and a busy events calendar.

Along Main Street there are lots of examples of ornate commercial architecture from the 19th century, typified by the Arcade Building from 1890, the American Block (1871) and The Spaulding Block (1872).

Things become especially refined along West Main Street, which is a historic district preserving some magnificent houses, and landmarks like the Westborough Public Library (1908) and the Evangelical Congregational Church (1834).

All set near the roundabout in the heart of downtown Westborough are eateries for Korean, Thai, Japanese, BBQ, pub fare, pizza and American diner food.

2. The Sibley House (Westborough Historical Society)

One of the opulent houses on Parkman Street just off West Main Street downtown is the headquarters of the Westborough Historical Society, founded 1889.

This is the Sibley House (No. 13), built by the wealthy blacksmith and wheelwright, William Sibley in 1844. His residence is in the prevailing Greek Revival style and he ran a wagon shop in an outbuilding on the property.

Sibley fought in the Civil War and was wounded at Battle of Antietam in 1862, before returning to become a successful sleighmaker in Westborough after the war.

The Sibley House was purchased by the historical society in 1990, and is a repository for its large decorative arts collections, as well as an exhibit space charting more than 300 years of local history.

3. Westborough Charm Bracelet Trail System

The town has a remarkable quantity of public open space preserved as conservation areas, and since 2000 there has been a long-term effort to link most of these up with a 28-mile trail loop.

At the time of writing, much of the Westborough Charm Bracelet Trail System had been completed, allowing you to traverse large swaths of the town on forest, cedar swamp or lakeside paths.

Lake Chauncy is especially scenic, and is home to the Town Beach in summer, restricted to residents of Westborough and Northborough.

There’s a lot of history to be discovered along the trails, with some of the town’s earliest roads, a stretch of the Boston and Worcester Street Railway (1903), centuries-old burial plots at Pine Grove and St. Luke’s Cemeteries, and Paleo-Indian sites at the Cedar Swamp Archeological District.

4. Cold Harbor Brewing

Less than half a mile from downtown Westborough on Milk Street, there’s a small-batch brewery that gets many of its ingredients from partner farms in the region.

Cold Harbor Brewing makes a whole spectrum of beers, but puts an emphasis on citrusy New England IPAs, with five varieties on tap when we compiled this list.

Typically there’s also a Stout (Milk Mustache), Golden Ale (Truell’s Gold), Brown Ale (Jackson Brown) and a Kolsch (Last Light).

The brewery is visited by a lineup of food trucks from the area, serving beer-appropriate bites like Indonesian street food, BBQ, hot dogs, brick oven pizza or burritos.

5. Harry’s Restaurant

Awaiting you on Route 9 in Westborough is an old-school American diner, family-owned and operated for nearly 80 years.

The menu is packed with homestyle dishes, from salads to pasta, burgers, sandwiches, shepherds pie, fried chicken, ribs, Italian roast beef and a lot more.

The speciality is New England-style seafood, and we’re talking lobster roll, lobster bisque, scallops, fish and chips (haddock), fried clams, the list goes on.

For a selection, try Harry’s Great Combo, which has a maritime medley of haddock, clam bellies, scallops, shrimp & calamari, with french fries, coleslaw and onion rings on the side.

A bestselling non-seafood dish loved by kids and grownups alike, is the macaroni & cheese, served as an entree with a homemade cheese sauce and cracker crumbs.

6. Crane Swamp

Not far from Lake Chauncy, the Westborough Charm Bracelet Trail System threads past a large area of cedar swampland in a 427-acre property.

As well as the ecologically rich swamp habitat, the trail from the lake beckons you through open fields, oak and forest, and a beautiful wet meadow.

As you go, keep an eye out for river otters and a resident pack of coyotes frolicking in the fields. Hunting is permitted all year (except on Sundays) in this area, so walkers are urged to wear orange here.

7. Whitehall State Park

On route 135, you can reach the Whitehall Reservoir in just a few minutes from downtown Westborough.

This 620-acre Great Pond has a secluded feel, and sits within an 837-acre state recreation area that was established in 1947 after the reservoir was decommissioned as a water source.

A hiking trail runs around the whole shore, and is about eight and a half miles long, so will take several hours to complete at a steady pace.

This is a sensational place for a kayaking trip, with little islands in the center that can only be approached from the water. The fishing is great too, with big numbers of trout and largemouth bass.

8. Bay State Green

Along Union Street in Downtown Westborough there’s an attractive green space, with paved trails, newly planted trees, benches, a small playground and a bandstand.

Bay State Green is the venue of choice for events and festivals during the summer, including the July 4th Block Party.

One recurring event is the long-running summer concert series, with family-friendly performances on Tuesday evenings in July and August.

Another is Screen on the Green, with outdoor movie shows in July, supported by local businesses, Uhlman’s Ice Cream and the BORO Sugar Shack, selling sweet treats. For both events you’re encouraged to bring a lawn chair or blanket.

9. Broken Creek Vineyard and Winery

On 40 acres, this family-owned vineyard and winery is in the Shrewsbury countryside, less than ten minutes from downtown Westborough.

The vineyard here was first planted in 2011, and was expanded through the 2010s, while a quaint old barn was converted into the winery.

This opened in 2015, and you can visit to enjoy a range of wines produced from Broken Creek’s estate-grown Cayuga White, Vignoles, Vidal Blanc, Traminette and Marquette Grapes, or grapes sourced from growers in California.

To sample a variety there’s a Wine Tasting option, or a flight of four 2 oz. pours. Fall is a fantastic time to visit the winery as you can take part in the harvest and watch an expert winemaker destemming and crushing the grapes.

10. Chestnut Hill Farm

The Trustees of Reservations manages one of the last working farms in the neighboring town of Southborough.

This is close to the line with Westborough and is a truly bucolic setting, with 170 acres of oak, maple and pine forests, rolling fields and pastures framed by historic stone walls.

Cart paths pass through a tapestry of habitats, from the wooded hillsides down to the edge of freshwater wetlands.

The farm has a certified-organic CSA program, but if you’re just passing through you can also call in at the farmstand for Trustees-grown meat, produce and eggs, as well as high-quality honey, preserves, dairy products, sauces and more from local producers.

11. Westborough Golf Club

Established on hilly ground in 1921, Westborough’s municipal 9-hole track has a great reputation, with notoriously quick greens and majestic views from its elevated tees.

There are four sets of tees, able to accommodate golfers of all standards, whether you want to play nine or eighteen holes.

The most memorable are the spectacular third hole, a dogleg par 5 with an elevated tee, and the seventh hole, which is a sharp downhill par 3, with views across Westborough from the tee.

12. Uhlman’s Ice Cream

This popular ice cream stand in Westborough is run by a family with a history in ice cream making going back to 1940.

Uhlman’s Ice Cream was founded as a farm stand in 1967, but was soon devoted to ice cream, and is now into its third generation of owners.

One of the special things about this place is the pastoral location, with dairy cows grazing in the field behind.

There are more than 70 hard ice cream flavors to choose from, as well as frozen yogurt, allergy friendly and no sugar added options, all with a huge choice of toppings, from whipped cream to cookie dough.

One of the signature flavors is the tangy but creamy Black Raspberry, which has a few fun variations, with oreo pieces, dark chocolate chip, and white and dark chocolate chunks (Purple Cow).

13. George H. Nichols Reservoir

Also incorporated into the Westborough Charm Bracelet Trail System is the George H. Nichols Reservoir, covering 313 acres and purchased in the 1960s by the state for flood control.

There’s a patchwork of town-owned properties, allowing the Charm Bracelet to connect a chain of trails tracing the shore, from Mill Pond School in the south, through Veterans Freedom Park in the east and past Westborough train station in the north.

You’ll find a parking lot for the trail by the station on the north shore. All of the trails at the reservoir have easy grades, suitable for cross-country skiing in the winter, and with a magnificent array of wildflowers in the summer.

14. FORE! Golf Entertainment

Over the road from Westborough Shopping Center on the Boston-Worcester Turnpike there’s a very different kind of golf experience.

The high-tech FORE! Golf Entertainment has state-of-the-art simulators that let you play dozens of the world’s iconic courses, from The Old Course at St Andrews to Pebble Beach Golf Links.

As well as giving avid golfers the chance to play the courses of their dreams, this is a great place to keep your game sharp through the Massachusetts winter, with a choice of scenic driving ranges.

FORE! Golf Entertainment doubles as a high-end sports bar, with HDTV screens all around, comforting pub fare and a long wine and beer list.

15. July 4th Block Party

Normally happening on the Friday before Independence Day, the July 4th Block Party is an endearing get-together downtown.

There’s usually a long double row of vendors down Main Street, with live performances and activities on Bay State Green.

Recent editions have offered a host of food options from local businesses and chains, as well as all kinds of fun for kids, with a dunk tank, hay and pony rides, inflatables and face painting.

One annual fixture is a show by The Reminisants, a local oldies covers band that has been going since 1973.