Sterling, Massachusetts, is a town of approximately 8,000 residents in Worcester County — one of the most genuinely charming and most historically distinctive small towns in north-central Massachusetts, incorporated in 1781 and carrying a cultural identity shaped by two pieces of American lore that give it an outsized national significance: the Sterling Center Common is the birthplace of the real “Mary Had a Little Lamb” — the actual girl, Mary Sawyer, whose pet lamb followed her to school and inspired the nursery rhyme — and the statue on the common commemorating that story was stolen, then replaced through a $26,000 community fundraiser, now secured so deeply it will never be taken again. Sterling’s landscape straddles the Wachusett Mountain corridor and the Nashua River watershed, giving it a combination of rolling orchard country, conservation forest, and genuine working-farm character that makes it one of the more picturesque agricultural communities in the region, and its Main Street village center — with a farmers market, beloved café, and excellent Mexican restaurant — retains a walkable small-town energy that larger neighboring communities have largely lost. Davis Farmland at 145 Redstone Hill Road is Sterling’s most comprehensively family-beloved and most enthusiastically praised destination — with a new big splash pad described as wonderful with plenty of space, shade, and bubbles, areas where animals run wild so visitors can go right up to pet and feed them, baby goats everywhere, pens with tortoises, baby cows, goats, and sheep, a camel, a reptile show, trampolines, rides, playgrounds, a BBQ place with delicious food, and bunny adoptions — described as solid gold and a grandpa’s favorite where Davis has proven itself the best among many farms and petting zoos visited, as a place where a first visit with an almost two-year-old granddaughter got her attention like nothing else with animals she could pet and feed right up close, and as truly wonderful and truly worth it if you can spend the day there with plenty for kids to do and so many animals to brush and pet. Sterling Center Historic District on the Sterling Common is the town’s most evocatively storied and most community-cherished historic landmark — with a weekly farmers market described as wonderful with plenty of shade and a well-maintained park, a statue memorializing the real Mary of “Mary Had a Little Lamb” fame, and a common described as the site of a true story that is not fake or just a fairy tale — described as a beloved place for a lifelong resident who grew up two miles away and knows the true story of Mary and her little lamb firsthand, as a wonderful weekly farmers market destination with plenty of shade and well-maintained grounds, and as a historically layered common where an hour can easily be spent looking at all the monuments and statues, especially during one of the festivals hosted there. Redemption Rock on Redemption Rock Trail in neighboring Princeton rounds out Sterling’s cultural picture as the region’s most historically consequential and most dramatically atmospheric geological landmark — open Wednesday, Thursday, Saturday, and Sunday from 9 AM with a large flat-top granite outcropping described as the second most important rock in American history only bested by Plymouth Rock, the site where Mary Rowlandson was ransomed and released after 11 weeks of captivity following the Lancaster Raid of 1676 for 20 pounds sterling, beautiful trails and lots of them, access to the Midstate Trail heading north toward Wachusett Mountain with nice views after 10-15 minutes, and a connection to one of the most fascinating stories in colonial New England — described as a trip back in time to colonial days where the story of Mary Rowlandson’s capture by the Wampanoag Nipmuc and Mohegan is fascinating, as a site with beautiful trails and lots of them offering excellent short-distance hiking from Redemption Rock to the top of Mount Wachusett, and as a historically loaded stumble of a discovery while hiking with the dogs.
Sterling’s outdoor landscape is anchored by its position at the eastern edge of the Wachusett Mountain corridor and threaded with conservation areas ranging from a beautiful roadside waterfall to access points for one of the finest state forest trail networks in Worcester County. Leominster State Forest accessible from Redemption Rock Trail in Sterling and Route 31 is the region’s most trail-rich and most ecologically varied state forest serving the Sterling area — open from 7:30 AM with highlights including the hike over Crow Hills, the hike to Rocky Pond, swimming at the beach on Crow Hills Pond, Crow Hills as a premier rock-climbing spot requiring a permit at the state forest headquarters, Paradise Pond as a great hike around the pond, the Redemption Rock to Crow Hill route via the Midstate Trail described as a nice trail system very clearly marked, and multiple parking areas off Route 31 — described as an excellent place to hike, bike, swim, and rock climb with highlights of the Crow Hills hike, the Rocky Pond hike, and a swim at the beach on Crow Hills Pond, as a place visited as often as once a week where Paradise Pond is always a great hike, and as a trail system with well-maintained and well-marked paths and a nice up-and-down trail with a cool little climb at the end. Rocky Brook Conservation Area on Beaman Road is Sterling’s most quietly beautiful and most road-trip-worthy local conservation stop — with a beautiful little waterfall and pond described as a perfect lunch stop on a long bike ride, trails described as seeming in good condition, a roadside waterfall and old foundation adding historical texture, and limited parking along the road giving it an off-the-beaten-path character — described as 100 percent recommended for stopping if you’re in the area with a beautiful little waterfall and pond, and as a nice roadside waterfall and old foundation worth a stop. Wachusett Mountain State Reservation at 345 Mountain Road in neighboring Princeton rounds out Sterling’s outdoor picture as the region’s most panoramically rewarding and most accessibly beloved mountain destination — open from 6:30 AM with spectacular tree colors described as perfect in fall, handicap parking at the very top for just a short walk up a paved path, a visitor center at the bottom with wonderful displays of animals and birds inhabiting the park, clean restrooms, friendly staff, well-maintained trails challenging due to rocks and uneven footing, nice views at the top, and an option to drive to the summit — described as a place where the trees’ colors are spectacular in fall and even elders can enjoy the summit via the short paved path from the handicap parking area, as a great escape where the hike to the summit was fun and manageable and the views from the top were absolutely worth it with miles of rolling hills and distant mountains visible on a clear day, and as a great spot for an easy and enjoyable hike perfect for dogs where the views from the top are beautiful and well worth the trip.
Sterling’s dining scene is anchored by one of the most beloved Mexican restaurants in all of Worcester County, a wonderfully cheerful Main Street breakfast café with a devoted following, and a well-regarded breakfast and lunch destination on Redemption Rock Trail that draws diners from throughout the region. The Brick Mexican Grill at 27 Main Street is Sterling’s most enthusiastically celebrated and most regionally acclaimed dining destination — open Monday through Thursday from 4 PM and Friday and Saturday from noon with the best Mexican food in the state according to one devoted reviewer where the food is fresh, flavorful, and perfectly prepared every time, burrito chile Colorado and Mexican pizza described as special, margaritas described as very good, a chocolate strawberry espresso martini and crème brûlée cheesecake special for Valentine’s Day described as incredible, Maria and team described as incredibly kind, accommodating, and genuinely caring, and server Erick described as so good — described as hands-down the best Mexican food in the state where Maria and team are incredibly kind and accommodating with amazing food and amazing people, as a special place with great food, great service, and great atmosphere where the burrito chile Colorado and Mexican pizza are must-orders and it’s a repeat repeat repeat destination, and as a place with awesome vibes and so good food with a server who was so good that visitors are totally planning on coming back. Emma’s Cafe at 37 Main Street is Sterling’s most warmly community-embraced and most creatively menu-driven breakfast and lunch café — open Monday and Wednesday through Friday from 7 AM and Saturday and Sunday from 8 AM to 2 PM with a breakfast steak quesadilla described as delicious with lots of flavor in the steak, a kicked-up hash with corned beef hash and sausage described as extremely flavorful, a blueberry lemonade described as to die for, a corned beef hash breakfast described as perfect balance of salty and savory with a massive portion made in-house, a Tuna Melt with potato salad described as phenomenal, a From Emma’s Garden omelet described as incredibly good having been ordered multiple times, and staff described as incredibly kind — described as surpassing all expectations with good price, good eating area, ease and efficiency of ordering, polite service, quality of food, and portion control at two meals for $20, as a place visited on a whim while passing through where everything was made in-house and the kindness of the employees was as memorable as the food, and as a place visited multiple times now with every visit leaving visitors in smiles having gotten the same order multiple times and loved it. Over Easy Cafe at 220 Redemption Rock Trail rounds out Sterling’s dining picture as the town’s most cozy and most consistently praised all-day breakfast destination — open Tuesday through Sunday from 7 AM with delicious food, warm and welcoming staff, a huge menu with both breakfast and lunch choices, hearty portions, a festive holiday-decorated atmosphere described as beautiful, server Jamie described as warm and friendly making the experience enjoyable, games for the kids as an adorable family-friendly touch, interesting items for sale from candy to art, and amazing-looking desserts — described as the only diner a traveling reviewer has gone back to twice on purpose where the food is delicious, the staff is warm and welcoming, the location is convenient, and the coffee is absolutely perfect, as a hidden gem that is cozy with friendly staff and an adorable atmosphere where food came quickly with hearty portions, and as a great place that is welcoming and friendly with a huge menu and good service along with good food.
