Real places, real neighborhoods and current market numbers, verified by broker Ryan C. Winslow.
What Sterling is known for
Sterling is the birthplace of Mary Sawyer, whose pet lamb inspired "Mary Had a Little Lamb," and a lamb statue stands on the Town Common. It is an apple and farm town known for orchards, Davis Farmland, the Davis Mega Maze and the Sterling Fair, which bills itself as New England's largest free fair.
The area was first settled around the Waushacum Lakes in the 1640s, and Gamaliel Beaman became the first permanent settler in 1720. The town, once called Chocksett, split from Lancaster and was incorporated as Sterling in 1781, named for William Alexander, Lord Stirling. The annual town fair began on the Town Common as a farm show in 1859, and Ebenezer Butterick developed his dress patterns here in 1863. Sterling is a small farm town of over 8,000 people where orchards, farm stands and conservation land sit between quiet roads and a compact historic center. Daily life runs on Main Street cafes, farm stores and quick highway access to Worcester and Leominster.
Where to live
The town center around the Town Common, the 1835 Town Hall and Pine Street, home to the Historical Society museum and Main Street spots like Emma's Cafe and The Brick. Compact village center. (source)
The lake area where the town's first settlers lived in the 1640s. The town maintains an easy, dog-friendly Waushacum Trail. (source)
The railroad-era section of town named for Lt. Joel Pratt, an aide to George Washington. The railroads reached Sterling in the 1850s. (source)
Orchard country, home to Meadowbrook Orchards and Rota Spring Farm. Rolling farmland with homes set along rural roads. (source)
Farm land worked by the Davis family since 1846, now home to Davis Farmland and the Davis Mega Maze. Rural roads and open fields. (source)
The north-south route toward Leominster with restaurants like Barber's Crossing North and the Black Sheep Tavern, plus quick access to I-190. (source)
Local favorites
Scratch kitchen and bar downtown since 2016. Known for ceviche, mariscada and handcrafted margaritas. (source)
Set in the former Bank Building on Main Street. Scratch soups, fresh scones and a signature turkey chili. (source)
A Worcester-born restaurant family (founded 1984) with its Sterling location on Route 12. Open seven days, with function space. (source)
The Chocksett Inn's restaurant, open to the public, with a changing seasonal menu, cocktails, local brews and a patio. (source)
Year-round breakfast and lunch on a family farm worked since 1912. Go for apple cider donuts, apple pie and David's BBQ sauce. (source)
Farm ice cream stand with seasonal flavors, a food menu, picnic tables and goats to feed. Farm store sells its own grass-fed beef. (source)
Family-owned since 1986, with dough made fresh daily. Pizzas, subs, salads and pastas. (source)
Local tavern on Route 12 with the slogan "Meet me at the Sheep." (source)
After hours
Four 18-hole layouts through the orchards and woods, open sunrise to sunset every day, with a pro shop on site. (source)
Fridays from 3 to 6:30 pm, May to October, at 1 Park Street. (source)
The historic green in the town center, home to the lamb statue and the original site of the town fair. (source)
Grab an ice cream, sit at a picnic table and let the kids pet and feed the goats. (source)
Active, family-friendly group at 1 Maple Street focused on local agriculture, community gardening and town involvement. (source)
Shopping
Independent gift shop on Main Street with handmade goods from U.S. artisans and Fair Trade makers. (source)
Home decor, furniture and gifts at 40 Main St, with interior design services. (source)
Garden center with plants, a stone yard, pond store and pottery, plus landscape design, delivery and installation. (source)
Farm store and bakery with house-made preserves, heat-and-serve entrees and pies to order. (source)
Seasonal fruits and vegetables, homemade breads and jams, and the farm's own grass-fed beef. (source)
Outdoors
Easy, scenic town trail. DCR runs public programs from 25 Gates Road, including a Halloween luminary walk. (source)
The 65 billion gallon reservoir has 37 miles of shoreline. Shore fishing in designated areas, walking and interpretive programs. No dogs, swimming or boating. (source)
19 acres of forest with a marked trail and views of the Wekepeke reservoir basin and farmland on Tuttle Road. (source)
19+ acres of fields, woods and a barn on Lucas Road by Stewart Pond, with trails into Leominster State Forest. (source)
Nearest state park. Hiking, mountain biking, the Midstate Trail, rock climbing at Crow Hill Ledges and swimming at Crow Hill Pond. (source)
3,000 acres around a 2,006-foot peak with 17 miles of trails and a summit road with 360 degree views. (source)
Federal refuge along the Nashua River with wetlands, oxbow ponds, trails and a kayak launch. (source)
Things to do
Family farm park on land the Davis family has farmed since 1846, known for rare and endangered livestock breeds, a focus that began with three highland cattle gifted after a 1990 fire, plus the Cowabunga Splash Park and U-pick apples. Built for kids 12 and under. (source)
Giant fall corn maze on Redstone Hill with more than 60 attractions, live entertainment and food. (source)
Statue on the Town Common honoring the lamb of Mary Sawyer, born in Sterling in 1806. (source)
Museum and research library at 7 Pine Street in the Sterling Center Historical District. (source)
Historic town hall in the center of town, one of Sterling's signature landmarks. (source)
On the calendar
All-volunteer agricultural fair with rides, horse, oxen and tractor pulls, livestock shows, an antique engine show and food. Roots go back to the Sterling Cattlemen's Association. (source)
The Halloween Mystery Mega Maze with trick-or-treating in the maze and dozens of attractions. (source)
Weekly market at 1 Park Street, 3 to 6:30 pm. (source)
DCR Wachusett Reservoir interpretive program starting at 25 Gates Road. (source)
Pick-your-own at Davis Farmland and Meadowbrook Orchards. (source)
Schools
Houghton Elementary School (Grades K-4, Sterling)
Chocksett Middle School (Grades 5-8, Sterling)
Wachusett Regional High School (Holden), Montachusett Regional Technical School (regional vocational option)
Listed for reference, not ranked. Confirm school zoning for any address with the district. (source)
Broker notes
I-190, Route 12, Route 62 and Route 140, with I-290 and I-495 nearby
Worcester Regional Airport, about 30 min; Boston Logan International Airport, about 75 min 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.