A must-visit and just steps from the Inn. This National Historic Landmark is a stunning "strawberry pink" Gothic Revival summer home. Guests can tour the house, explore the 1850s parterre gardens, and see the oldest surviving indoor bowling alley in the U.S.

Take a stroll around the Common. The area features the 1821 Congregational Church and the historic Woodstock Academy.

A small, serene botanical park right on Woodstock Hill, perfect for a quick, peaceful walk among labeled trees and shrubs.

Technically just over the line in Danielson, this is a world-famous destination. It's a series of historic greenhouses (some dating back to 1892) filled with rare tropical plants. Guests can see a 120-year-old lemon tree that grows lemons the size of grapefruits. It's a "jungle" experience in the middle of New England.

For guests who want a bit of adventure and folklore, this park is home to the cave where General Israel Putnam famously fought a wolf in 1742. There are great hiking trails ranging from easy to moderate.

Also known as Levi's Mill Bridge, this distinctive landmark is nestled in Brooklyn, Windham County. Spanning the tranquil Blackwell Brook, this modern covered bridge, constructed in 2010, holds the unique distinction of being the only one of its kind in Northeastern Connecticut. Visitors consistently praise the bridge's serene setting on a quiet back road, surrounded by pristine countryside.

The winery offers tastings on a beautiful 40-acre farm, while the brewery right next door has a rotating selection of craft beers, a fire pit, and often hosts food trucks.

Home to the famous Ballet of Angels wine, offering award-winning wine tastings and an upscale restaurant with sweeping vineyard views.

Tucked away in a rustic setting surrounded by pastoral views of grazing horses, this unpretentious, winemaker-driven boutique winery focuses on small-batch production. Rather than growing local grapes, they craft balanced, clean wines using carefully selected grapes imported from top regions worldwide (like Italy, Chile, and California). With relaxed indoor and outdoor seating, live weekend music, and a warm, casual vibe, it's a wonderful spot to slow down and enjoy a glass.

A beautiful working fruit orchard and farm stand located directly along the Air Line State Park Trail.

A great stop for seasonal fruit picking (September is a great month for a variety of apples) or visiting their Bakery Barn for fresh apple cider donuts and local pies.

A working bison farm offering seasonal wagon rides to see the herd, plus a farm store with unique local goods.

Not to be confused with the cottage, this park sits on Roseland Lake. It's perfect for guests who want to go for a jog, use the playground, or launch a kayak. It also features a golf course and a driving range.

About a 15-minute drive away, this park offers deeper hiking into the woods and scenic views of Mashapaug Lake — ideal for the more active guests in the group.

Miles of walking trails winding through rare grassland habitats — a top regional birdwatching hotspot.

A gravel rail-trail built on an 1870s railroad bed — flat, scenic, and perfect for a long walk or bike ride.

Peaceful, rugged trails through pine forests and along the river, ideal for hiking and birdwatching.

This is one of the most beautiful roads in New England. Drive south toward Pomfret to see rolling farmlands, stone walls, and historic architecture.

A massive multi-dealer antique center housed in an old blacksmith shop. It's a great place for guests to browse for unique New England treasures.

In "the Next Town Over," downtown Putnam is known for its "Antique District" — a multi-block town center lined with antique shops, art galleries, and independent boutiques.

Located right on the border in Brooklyn, CT (on Providence Road), this charming specialty market is a favorite local stop for fresh produce, prepared gourmet foods, artisan baked goods, and regional farm products. It's an ideal place for guests to grab a quick lunch, pick up local snacks, or browse New England food gifts. Our favorite sandwich and cookie shop!!!

Located right down the road from the Inn at Woodstock Hill (on Route 171), this charming full-service bakery is known for its wide selection of freshly baked artisan breads, pastries, custom cakes, and sweet treats. It's a great morning spot to grab a cup of coffee, a fresh muffin or croissant, and sit in their cozy seating area. They are also well-regarded locally for offering accommodating options like vegan and gluten-free baked goods.

A legendary local haunt for coffee, scratch-made baked goods, hearty sandwiches, soups, and live acoustic music.

For guests who want to find live music and a lively pub vibe. They offer an eclectic menu of pub fare alongside a large selection of craft beers. Open late until 1:00 AM most nights, making it a good choice for a late-night hangout spot.

A spacious, welcoming spot specializing in BBQ, burgers, and hearty American comfort food.

A classic New England "country breakfast" spot that also features a driving range on-site.

An approachable sit-down spot for steaks, seafood, and American classics with a nice outdoor deck.

A beloved Quiet Corner staple since 1990, this family-owned farm stand serves ultra-creamy, small-batch ice cream (a rich 16% butterfat recipe) with dozens of rotating seasonal flavors. Set on a historic farm on Hampton Road, guests can enjoy fresh-waffle-cone sundaes, frappes, and classic treats at outdoor picnic tables. In addition to ice cream, the farm produces its own 100% pure Connecticut maple syrup and pasture-raised meats.