Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Upton is known for
Upton is known for the 2,660-acre Upton State Forest, where Civilian Conservation Corps buildings from the Great Depression still stand. It is also home to the Upton Chamber, a domed stone cave off Elm Street that is one of the largest of roughly 300 stone chambers in the Northeast. The town manages about 1,200 acres of conservation land laced with marked trails.
Upton was incorporated in June 1735 from parts of Hopkinton, Mendon, Uxbridge and Sutton. Boots and shoes drove the economy for about 100 years, and in 1837 Upton factories made 21.7% of all boots produced in Worcester County. From 1860 William Knowlton grew small shops into what was long considered the largest hat industry in the world, and the Grafton and Upton Railroad arrived in 1873. Upton is a small open town meeting community of about 8,000 people (2020 census) about 35 miles west of Boston. Daily life centers on the town common, Main and Milford Streets, the Community Center and a long list of town trails and ponds.
Where to live
The historic village around the town common, Main Street and Milford Street, with Town Hall at 1 Main Street, the 1848 Holy Angels church building and a cluster of shops and restaurants. The town has a master plan underway for the common and the nearby Knowlton Risteen property. (source)
The area along West Main Street, home to Red Rock Grill and Bar. A town working group produced the West Upton Center Plan in 2025 to guide future village-style growth here. (source)
The rolling northwest section of town around Warren Brook, which locals call Forest Green for the hills seen from Fowler and Mechanic Streets. It borders Upton State Forest and the Whitney, Warren Brook and Howarth conservation areas, so many homes back up to trails. (source)
The neighborhood around Pratt Pond near School Street and North Main Street. The Kiwanis Beach and Pratt Pond Conservation Area trailheads are here, and Kiwanis Beach has the town beach plus ball fields, tennis and basketball courts and a pavilion. (source)
A quiet stretch near the eastern shore of Mill Pond anchored by Heritage Park, the seven-acre town park at 18 Elm Street that protects the Upton Chamber stone cave. (source)
The renovated 19th-century hat factory in town is now affordable senior housing with 89 units, letting many longtime Upton seniors stay in town. (source)
Local favorites
Full lunch and dinner menu plus Sunday brunch; the old fashioneds and fish tacos get regular praise. (source)
Known for birria tacos, ceviche and fajitas with a tequila bar and catering. (source)
Casual pub with burgers, pizza, seafood combos and hand-cut fries, plus catering. (source)
Local favorite with a long flavor list; Graham Central Station and toasted coconut are customer picks. (source)
Coffee, bagel breakfast sandwiches, subs, soups and salads; it also has a Sutton location. (source)
Neighborhood deli that locals go to for Italian steak tips. (source)
House special pizza, Greek calzones and steak and cheese subs, with online ordering. (source)
Pizza, calzones and Syrian pocket sandwiches; gluten-free pizza is available. (source)
After hours
Community nanobrewery taproom at 8 Grove Street in Upton center, founded by childhood friends Mike Rushford, Brian Goodman and Eric Martin. Trivia runs Wednesday and Thursday nights at 7. (source)
Cafe run by The United Parish of Upton at 1 Church Street since June 2021, with free wifi, puzzles and space for groups. Open Tuesday to Saturday mornings. (source)
The Community Center at 9 Milford Street holds the Upton Town Library and The Upton Center senior center, with book groups, storytimes, museum passes and a Library of Things. (source)
The town beach on Pratt Pond, with baseball, soccer and lacrosse fields, tennis and basketball courts and a pavilion. Resident and non-resident beach passes are sold at the gate. (source)
Public golf club at 91 Clubhouse Lane in neighboring Northbridge with weekly leagues, a short course, a practice range and a restaurant. (source)
Shopping
Independent record store that has served Upton for 18 years, buying and selling vinyl. It has since added a second store in Burlington, CT. (source)
Upton florist open seven days a week with daily delivery, seasonal arrangements from local and organic blooms, wedding flowers and a boutique of clothing, jewelry and bath goods. (source)
Pick-your-own fruit farm at 234 Ball Street in Northborough with a farm store, bakery, apple cider donuts and seasonal strawberries, peaches, apples and pumpkins. (source)
Full-size Wegmans supermarket at 9102 Shops Way in Northborough, open 6 am to midnight, with a pharmacy and prepared meals. (source)
Outdoors
2,660-acre state forest at 205 Westboro Road with Civilian Conservation Corps buildings from Camp SP-25, a 2-mile Healthy Heart Trail, and trails for hiking, mountain biking, horseback riding and cross-country skiing. (source)
Town conservation land with the Walleston Trail (3.25 miles, strenuous) and Rockwood Meadows loop (2.4 miles), both part of the town's Hike Upton Challenge. (source)
Linked North Upton preserves. The 63-acre Whitney parcel was part of a mid-1700s farm tied to Eli Whitney's family, and its Porier Path connects Upton State Forest to the Warren Brook Watershed trails. (source)
1,500-acre park at 164 Cedar Street in Hopkinton with two seasonal swimming beaches, boating, kayaking and more than 10 miles of trails. (source)
Granite chasm at 198 Purgatory Road in Sutton with rock formations such as The Corn Crib, The Coffin and Lovers' Leap, plus 2 miles of trails and rock climbing. (source)
Refuge created in 2000 on more than 2,000 acres of former Army land, with over 15 miles of trails for hiking, biking, fishing and cross-country skiing. (source)
National park telling the story of the American Industrial Revolution, with sites including the Little Red Shop in Hopedale and Old Slater Mill in Pawtucket, RI. (source)
Things to do
A 14-foot tunnel leads into a hillside to a beehive-shaped stone chamber about 12 feet across and 11 feet high. Its origin is still debated, and the town bought the seven-acre site at 18 Elm Street with Community Preservation Act funds. (source)
Remaining buildings from a Civilian Conservation Corps camp, preserved and interpreted by the Friends of Upton State Forest. (source)
Town challenge of 10 mapped hikes on town-owned land. Finish any 6 to earn a Hike Upton pin or patch. (source)
Family-owned zoo at 2 Southwick Street in Mendon with more than 900 animals on over 200 acres. (source)
Seasonal twin-screen drive-in movie theater at 35 Milford Street in Mendon with a snack bar and special events. (source)
On the calendar
The Friends of Upton State Forest hold a volunteer trail work party for National Public Lands Day, plus another each spring. (source)
Annual holiday bazaar at The United Parish of Upton. The 2026 date is Saturday, December 5, 10 am to 3 pm. (source)
The Upton Town Library's annual overnight where kids leave stuffed animals for a night in the stacks and a bedtime story. (source)
Free guided walks and events on Upton's conservation land, open to all ages. (source)
Schools
Memorial School
Miscoe Hill School
Nipmuc Regional High School, Blackstone Valley Regional Vocational Technical High School
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
Route 140 runs through town toward Milford and Worcester (via Route 122), with I-495, Route 9, the Mass Pike (I-90) and Route 146 reachable nearby.
Worcester Regional Airport (about 40 min), Boston Logan International (about 1 hr), and T.F. Green in Warwick, RI (about 1 hr), 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.