Oakham MassachusettsATTRACTIONS & THINGS TO DO


Listed below are the best attractions and things to do near Oakham, Massachusetts.



1. Agronomy Farm Vineyard

LOCAL WINES AND VIEWS


Agronomy Farm Vineyard invites guests to experience wine tastings among the rolling hills of Oakham. Visitors can sample a variety of locally crafted wines while enjoying panoramic views of the countryside. The vineyard often hosts events such as 'Wine Downs' and seasonal activities, making it a favorite spot for locals and tourists.


2. Quail Hollow Golf Club

SCENIC GOLF EXPERIENCE


Quail Hollow Golf Club offers golfers a picturesque New England golfing experience in Oakham. The course presents a challenging terrain suitable for both beginners and seasoned players. The club is popular for its well-maintained greens and welcoming clubhouse atmosphere.


3. Oakham Historical Museum

LOCAL HERITAGE EXHIBITS


The Oakham Historical Museum preserves and showcases the rich history of the town through exhibits and artifacts. Visitors can learn about Oakham's founding, community events, and notable residents. The museum is a key destination for those interested in local culture and stories.


4. Mass Central Rail Trail

HIKING AND BIKING PATH


The Mass Central Rail Trail runs just outside Oakham, providing over 25 miles of scenic trails ideal for walking, jogging, and cycling. The trail meanders through picturesque woodlands and offers ample opportunities for wildlife observation. It is easily accessible by bike or car from the town center.


5. Brookfield Orchards

APPLE PICKING AND SHOP


Brookfield Orchards, a short drive from Oakham, is cherished for its apple picking, fresh donuts, and old-fashioned country store. Visitors can enjoy seasonal pick-your-own experiences or shop for local apple products and baked goods. The orchard is a family-friendly destination, especially popular in the fall.



6. Quabbin Reservoir

NATURE AND WILDLIFE HAVEN


Quabbin Reservoir, the largest inland body of water in Massachusetts, is located near Oakham and serves as a vast wildlife sanctuary. The area features hiking trails, scenic overlooks, and opportunities to spot bald eagles and other wildlife. It is a favorite destination for nature lovers and photographers.


7. Hardwick Winery

COUNTRYSIDE WINE TASTINGS


Hardwick Winery, set among the scenic fields of Central Massachusetts, offers visitors a variety of handcrafted wines in a welcoming tasting room. The winery organizes tours, vineyard events, and a charming rural experience. Guests often enjoy relaxing on the outdoor decks with a glass of wine in hand.


8. Brimfield Antique Flea Market

LARGEST OUTDOOR ANTIQUES MARKET


The Brimfield Antique Flea Market is renowned as America's oldest and largest outdoor antiques show, attracting collectors and enthusiasts from all over the country. The event is held three times a year and features thousands of dealers with a wide array of treasures. Visitors can browse stalls for antiques, collectibles, and unique finds.


9. Pine Acres Family Camping Resort

FAMILY CAMPING GETAWAY


Pine Acres Family Camping Resort offers a full-service camping experience with amenities like waterfront sites, playgrounds, and recreational activities. The resort features a lake for swimming and boating, plus seasonal entertainment for all ages. It's a popular choice for family vacations near Oakham.


10. Rutland State Park

OUTDOOR RECREATION AREA


Rutland State Park, located close to Oakham, features a large freshwater lake, picnic areas, and miles of hiking trails. The park is ideal for swimming, fishing, picnicking, and enjoying natural landscapes. Its proximity and amenities make it a go-to spot for outdoor enthusiasts.



11. Rose32 Bread

ARTISAN BAKERY AND CAFE


Rose32 Bread is famed for its artisan breads, breakfast options, and locally sourced sandwiches in a rustic, inviting setting. The bakery is a favorite stop for travelers and locals seeking fresh pastries and casual daytime meals. The shop also offers retail products like jams and fine cheeses.


12. The Clam Box

CLASSIC NEW ENGLAND SEAFOOD


The Clam Box in Brookfield is a beloved seafood shack known for its fried clams, lobster rolls, and casual atmosphere. The eatery offers indoor and outdoor dining and is especially busy during the summer months. Their classic offerings and friendly service make it a regional favorite.


13. Old Sturbridge Village

LIVING HISTORY MUSEUM


Old Sturbridge Village is a renowned living history museum depicting life in an early 19th-century New England town. Guests can explore historic buildings, watch live demonstrations, and interact with costumed interpreters. The immersive exhibits provide insight into daily life, trades, and culture of the era.


14. Rapscallion Brewery

LOCAL CRAFT BEERS


Rapscallion Brewery offers a welcoming taproom atmosphere with a variety of house-brewed craft beers and a small menu of pub fare. The brewery frequently hosts live music, events, and community gatherings. It's a favorite meeting spot for craft beer enthusiasts near Oakham.


15. Hodgkins School Marketplace

ANTIQUES AND COLLECTIBLES SHOPPING


Hodgkins School Marketplace features a wide array of antiques, vintage goods, and unique collectibles in a historic former school building. Shoppers can browse room after room of dealer booths, each offering a distinct selection. The marketplace is a treasure trove for anyone interested in history and rare finds.