Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Westborough is known for
Westborough is the birthplace of Eli Whitney, inventor of the cotton gin, and holds the headwaters of the Sudbury and Assabet rivers. It sits where the Mass Pike (I-90) meets I-495, with its own MBTA commuter rail stop. Locals know it for Route 9 institutions like Harry's Restaurant, in business since 1946.
Westborough was settled in 1675 and incorporated in 1717 as the 100th town in Massachusetts. Eli Whitney was born here in 1765, and the Boston-Worcester railroad reached town in 1834, turning farms into a manufacturing center. In the 1870s the National Straw Works on East Main Street was the largest straw hat maker in the country. About 21,500 people live here (2020 census), many commuting to Boston, Worcester or the office parks along Route 9 and I-495. Daily life mixes a walkable downtown rotary, wooded conservation trails and summer days at Lake Chauncy.
Where to live
The town center where Route 30 (Main Street) and Route 135 (South and Milk Streets) meet at a rotary. Older homes, small shops and restaurants sit close together. Town Meeting voted in March 2026 to consolidate the downtown zoning districts into one base district, pending Attorney General review. (source)
A 20-acre residential district just east of the town center, listed on the National Register of Historic Places in 2006. It holds about 80 modest houses on small lots, mostly built between 1860 and 1890, on streets including Cottage, Elm, Spruce, Green, Pine and South. (source)
Homes near Westborough's 182-acre lake. The lake has a public beach for Westborough and Northborough residents, with lifeguards back on duty starting in the 2026 season. (source)
The commercial spine of town with plazas, hotels and office parks. In March 2026 the Planning Board approved a 388-unit, five-story apartment project on both sides of Route 9 near Route 135 (171 Milk Street and 222 Turnpike Road). (source)
The area around the MBTA commuter rail station at Smith Parkway and Fisher Street, on the Framingham/Worcester Line. The station lot has 448 parking spaces, a draw for Boston commuters. (source)
Local favorites
Family owned since 1946 and on Route 9 in Westborough since 1969. Known for breakfast all day, lobster rolls, fried clams and lobster bisque. It celebrated 80 years in June 2026. (source)
A Westborough stop since 1967, making small-batch ice cream with a 14% butterfat recipe. Staffed by about 85 local high school and college scoopers. (source)
Three concepts under one roof: traditional Chinese at Cheng Du, Japanese kushiyaki grill at Akamon and the 157 Bin wine bar and lounge. (source)
A sit-down Italian spot downtown that takes reservations. Closed Sundays. (source)
Wings and barbecue plus burgers and craft beer, with dine-in, takeout and delivery. (source)
Weekday lunch and dinner Thai just off Route 9 near I-495. Gluten-free versions of dishes can be made on request. (source)
Opened September 5, 2026 as the chain's first Massachusetts location. Dozens of Indian dishes with adjustable spice levels, plus desserts and juices made fresh daily. (source)
The second location of a Marlborough family restaurant, opened in 2026. Comfort food, cocktails and weekend brunch. (source)
After hours
The cafe for Upton-based Red Barn, serving fresh coffee and baked goods downtown at 17 South Street. Open daily from early morning. (source)
Irish-style pub at 17 Connector Road, open until 12:30 a.m. most nights, with a function space for parties. (source)
A wine bar and lounge inside the Cheng Du building on Route 9. (source)
Nonprofit coffee, breakfast and lunch cafe off Route 9, opened in 2026. It doubles as a job training program run by MAB Community Services for people with disabilities. (source)
Ice rink at 15 Bridle Lane used for skating and hockey. (source)
Shopping
Plaza at Route 9 and Lyman Street with Super Stop & Shop, Staples, Tatnuck Bookseller, Julio's Liquors, local shops and several restaurants. (source)
Independent bookstore, gift shop and breakfast and lunch cafe at 18 Lyman Street, with author events. (source)
Wine, beer and spirits shop in the Westborough Shopping Center that hosts tastings, including a Sake Day celebration with nearly 100 sakes in October 2026. (source)
Farm stand at 80 Jasper Street on a family farm working the land since 1722. Sells fresh fruit, vegetables and farm products, and runs a fall CSA. (source)
Toy and game shop in the Westborough Shopping Center. (source)
Outdoors
182-acre lake with a town beach for Westborough and Northborough residents, plus swimming, boating and fishing. (source)
63 acres owned by Sudbury Valley Trustees with stone walls, woods, fields, several trail loops and an old cattle underpass beneath the former trolley line. (source)
Walking area around a reservoir that supplies part of the town's drinking water. Dogs must be leashed or under electric-collar control. (source)
Nearly 2,800-acre state forest, mostly in Upton with smaller sections in Hopkinton and Westborough. It includes the last remaining Civilian Conservation Corps camp in Massachusetts. Nearest state park land. (source)
State park created in 1947 around the former Hopkinton Reservoir, managed by the Department of Conservation and Recreation. (source)
Former U.S. Army land transferred to the U.S. Fish and Wildlife Service in 2000, with over 15 miles of trails for hiking, biking, fishing and cross-country skiing. (source)
National Park Service unit in Massachusetts and Rhode Island that tells the story of the early American Industrial Revolution and its textile mills. (source)
Things to do
Family farm since 1722 with seasonal pick-your-own raspberries, flowers and pumpkins, a farm store and a food truck. (source)
Local history group founded in 1889. Holds free programs and a history book group at the Sibley House, 13 Parkman Street. (source)
Trampoline and family entertainment park at 290 Turnpike Road with toddler time, teen glow nights and birthday parties. (source)
Library founded in 1857, returning to its renovated building at 55 West Main Street with reopening planned for November 2026. (source)
A walkable National Register district of 1860s to 1890s homes just east of downtown. (source)
On the calendar
Parade along South Street ending with a ceremony at the Forbes Memorial Building, followed by refreshments from VFW Post 9013. (source)
Town block party with flags, speakers and community groups. The 2026 edition marked America's 250th anniversary. (source)
Weekly market at Bay State Commons, with mascots Miss Blue and Mr. Maize at the rotary and a Power of Produce Club for kids. (source)
Farm tasting event set for Sunday, October 18, 2026, with proceeds going to the Westborough Food Pantry. (source)
Schools
Armstrong Elementary School (K-3), Annie E. Fales Elementary School (K-3), Hastings Elementary School (K-3), Mill Pond School (grades 4-6)
Sarah W. Gibbons Middle School (grades 7-8)
Westborough High School
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
I-90 (Mass Pike) and I-495 meet at the east edge of town. Route 9 carries most of the retail and office traffic, and Routes 30 and 135 meet at the downtown rotary. MBTA commuter rail stops at Westborough station on the Framingham/Worcester Line.
Worcester Regional Airport (ORH): about 30 minutes. Boston Logan International (BOS): about 50 minutes without traffic.
Ryan C. Winslow, broker/owner of Winslow Homes. REALTOR® since 2009, 3,000+ homes sold, broker in FL, MA, CT and RI, U.S. Army Retired.
Researched and verified 2026-09-28. Businesses change; call ahead.