Looking for a charming getaway packed with local flavor, scenic views, and plenty to explore? Holliston, Massachusetts, offers a unique blend of classic New England charm and modern-day conveniences, making it the perfect place to relax and enjoy the best of MetroWest. Whether you’re hiking the Upper Charles Rail Trail, indulging in local treats, or checking out the town’s unique shops, Holliston invites you to unwind, and enjoy a taste of small-town life with big-hearted hospitality.
Begin your weekend by exploring the Upper Charles Rail Trail, a scenic path perfect for biking, jogging, or leisurely walks and great for wildlife spotting. The trail connects Holliston to neighboring towns and offers picturesque views, making it a favorite for both locals and visitors. Blair Square, right on the trail, is a popular gathering spot and hosts seasonal events, concerts, and picnics. It’s a delightful place to spend a few hours relaxing and enjoying the vibe.
No visit to Holliston is complete without a stop at Out Post Farm. This family-owned farm stand and restaurant offers a variety of fresh, homegrown produce, baked goods, and hearty meals. During the Summer, their “Smoker Tuesdays” feature smoked brisket, turkey, ribs, and pulled pork, while “BBQ Thursdays” serve up half-chicken dinners with all the fixings. Don’t miss their daily sandwiches, including the popular “Gobbler” with freshly roasted turkey breast. For a taste of local flavor, you can’t miss TC Scoops, a beloved ice cream spot offering up delicious confectionary delights and nostalgic favorites. They challenge you to name a topping they don’t offer!
The town’s historic downtown offers a lovely collection of boutiques, cafes, and local shops. Aesop’s Fable bookstore is ideal for picking up your next read, while Bird and Bear offers modern home décor and unique gift items. For something sweet, The Candy Cottage is your go-to spot for candy and treats, while The Grapevine Gift Shop is filled with locally-made artisan goods and handcrafted gifts.
Swing by Boston Honey Company, a family-owned apiary, for a sweet and sunny stop. Sample their amazing raw honey, browse a shop full of beeswax candles and honey-based gifts, and don’t miss the observation hive where you can watch bees at work up close. Grab a honey-infused ice cream, challenge your crew to a lawn game, and soak up the beautiful views—it’s a hidden gem for families, foodies, and curious travelers alike!
Holliston is home to a thriving art scene, and Cheryl Cohen Mosaics is a must-visit for art lovers. You can view her stunning mosaics and even sign up for a hands-on class. If you’re in town on a Tuesday afternoon, don’t miss the Holliston Farmers Market at the Old Mill Building, where you can pick up fresh produce, local baked goods, and handcrafted items. The Old Mill also features open artists’ lofts on Saturdays and offers WSK, a commercial kitchen space that hosts culinary classes and pop-up events.
Golf enthusiasts can spend a day at Pinecrest Golf Club, an 18-hole municipal course offering a driving range, putting green, and a restaurant. It’s a great spot for both casual play and events.
End your day at Casey’s Pub, a laid-back local favorite in Holliston’s historic Mudville neighborhood. Believed by many to be the inspiration for the famous poem Casey at the Bat, Mudville gives this pub a special place in baseball folklore. Enjoy hearty comfort food, a cold drink, and a bit of local legend—all in one stop.
Whether you’re visiting for a few hours or staying for the weekend, it’s easy to see why so many visitors return—and why locals are proud to call it home.
