The Overlook is a unique campus with hundreds of acres in the heart of New England, including 16 miles of trails for walking, hiking and cross-country skiing – not what you might expect from a “retirement community.”

In addition to a beautiful, vast setting to explore, The Overlook’s convenient Charlton location keeps people within close reach of their favorite outdoor activities available at nearby state parks. Hike or cross-country ski through a forest trail, fish for trout on a nearby lake, build a fire and camp out under the stars and more. There are countless opportunities to enjoy nature’s bounty! Here are a few of our favorite central Massachusetts state parks and other outdoor adventures.

Spencer State Forest

Located to the north just off Route 31/Charlton Road, Spencer State Forest is less than a 15-minute drive from The Overlook. This Massachusetts state park boasts 965 acres of woods, rivers and trails – including 92 miles of the Midstate Trail that runs between Massachusetts’s Rhode Island and New Hampshire borders. It’s perfect for an adventure-filled day trip or weekend getaway, where you can picnic or go kayaking or canoeing, horseback riding, hunting, and snowshoeing.

While you’re in Spencer, we encourage you to stop by the Spencer Trappist Brewery for a beer and to learn about how monks use sustainable practices in their approach to brewing.

Moore State Park     

In the town of Paxton about 30 minutes north of The Overlook, history buffs will especially love Moore State Park. In the 18th and 19th centuries, it was a mill village with watermills powered by the lovely Turkey Hill Brook, where water falls 90 feet downward over a 400-foot run, according to Discover Central Massachusetts. You can still get a feel for what life was like back then, as some odds and ends remain, like an old schoolhouse, tavern and quarry.

A popular trail that is less than 2 miles and appropriate for all skill levels is the Old Bringham Road Trail, part of which runs along Eames Pond. Bring your neighbor, dog or grandkids along to see blooming wildflowers, ponds, waterfalls, critters and more. Don’t forget the sunscreen and bug spray!                                                             

Oakham State Forest

This 650-acre forest is right next to the Treasure Valley Scout Reservation. Hike a few miles on the eastern side and you’ll come across Sampson’s Pebble, an enormous glacier erratic on top of a hill, marking the path of prehistoric glacier movement.

Outdoor Attractions in Worcester and Sturbridge

In addition to beautiful Massachusetts state parks, many outdoor and cultural activities are available to enjoy in nearby Worcester and Sturbridge.

In Worcester, visit Broad Meadow Brook, the largest urban wildlife sanctuary in New England. You can go on a guided bird walk and learn about migration patterns and conservation efforts. The spectacular Bancroft Tower is a historic castle-like structure built in the 1900s using large stones. Green Hill Park is a Massachusetts Vietnam Memorial with serene walking paths that overlook the city.

In Sturbridge, step back in time at the Old Sturbridge Village, where you can interact with historians dressed in 19th-century costumes and learn about simpler days. Forty antique restored buildings showcase rural New England life in the 1830s, including a cider mill, print shop, bank, sawmill and blacksmith shop. Bring the grandkids for this perfect family outing. 

Explore the Great Outdoors Right Here at The Overlook

Henry David Thoreau said, “Wildness is the preservation of the world.” The beauty of living at The Overlook is that you don’t have to go far to connect with nature. With 450 acres of unspoiled New England countryside, it’s easy to immerse yourself in wildlife. The Overlook is like having your very own Massachusetts state park in which to relish and get lost. Your future looks great from here!

Skip to content