Things to do in Pomfret CT: Top 15 Most Unique Spots

For classic New England charm, Pomfret, CT is your spot. Rolling hills, winding country roads, old stone walls, and a bunch of cool shops and restaurants makes Pomfret worth a visit. And all their many attractions are tucked into one of Connecticut’s oldest towns (since 1713!). Pomfret has that perfect mix of rural charm and history that makes you feel like you’ve gone back a century or two—but with better food and wine.

Get into hiking, wine tasting, or just soaking up nature, here. Pomfret’s spot in the Last Green Valley is ideal. The town leans into keeping things laid-back and scenic, with an eclectic collection of attractions. So if you’re into unplugging and enjoying the simple pleasures, you’ll love it here.

Ready to discover the best things to do in Pomfret CT? Let’s get into it:

Quick Hits

• History Buffs: Pomfret’s got roots all the way back to the 1600s.

• Outdoor Lovers: Trails, parks, and scenic views are everywhere.

• Unique Finds: Historic landmarks, vineyards, and more.

• Shop & Dine: Handmade goods, cozy cafés, and local flavors.

A Brief History of Pomfret CT

Pomfret’s been around since the 1600s, back when Native tribes like the Nipmucks called it home. Major James Fitch bought the land in 1686, sold it off to settlers, and by 1713, Pomfret was an official town. The name comes from Pontefract, England.

As the years went by, Pomfret grew as a quiet, rural community. It had its ups and downs, especially in the 1800s when folks left for industrial towns. But it stayed true to its roots, keeping its small-town rural environment and charm intact. By the late 1800s, Pomfret became a retreat for the well-to-do, and it’s still popular for its peaceful vibe today. If you’re a fan of history, nature, and a bit of New England charm, Pomfret’s your place!

Best Things to do in Pomfret CT

Whether you’re into outdoor adventures, sipping local wine, or just soaking up some good ol’ New England charm, this town has plenty to do. Read on for some of the best things to do when you find yourself in Pomfret, CT.

• Airline State Park Trail: Perfect for hiking or biking along an old railway with stunning countryside views. Don’t forget your camera!

• Mashamoquet Brook State Park: Scenic hikes, picnic spots, and Wolf’s Den, where the last wolf in Connecticut was killed. Great for a day of exploring or relaxing.

• Sharpe Hill Vineyard: Local wine with a view! Grab a glass of their popular Ballet of Angels and enjoy the peaceful CT vineyard setting.

• Connecticut Audubon Center: Ideal for birdwatching and nature walks. Explore trails and learn about local wildlife conservation.

• Frog Rock: A quirky stop featuring a rock shaped like a frog. Fun for a quick photo op, especially for kids.

• Diana’s Pool: A hidden swimming spot surrounded by nature, perfect for cooling off on a hot day.

• Woodstock Fair: Held in late summer in nearby Woodstock, this classic fair features rides, games, food, and agricultural exhibits—fun for all ages.

• Tree House Orchard & Farm: Pick your own fruit year-round with activities for all ages. Great for apple-picking in the fall.

• Lapsley Orchard: A family farm with 24 apple varieties, pumpkins, berries, and more. Pick-your-own fun at this CT apple orchard starts in September.

• Bara-Hack: After an increase in paranormal tourism, the private owners of the land on which this sits closed-off access to this spot. But this abandoned village is one of the most haunted places in Connecticut, though today you’d need special permission or be with a tour group to see it.

Historic Sites in Pomfret Center

For history buffs—or fans of old buildings with cool stories—Pomfret’s got plenty of CT historic sites. This little town has many attractions on the National Register of Historic Places:

• Pomfret Street Historic District: Stretching across 380 acres along Route 169, this area is packed with historic homes and buildings.

• Brayton Grist Mill: Located right off US 44, this old mill was added to the National Register in 1986.

• Gwyn Careg: Also on US 44, this stunning estate made the list in 1994. If you love classic architecture and lush gardens, this place will catch your eye.

• Israel Putnam Wolf Den: Now part of Mashamoquet Brook State Park, this is where Israel Putnam famously killed the last wolf in Connecticut. It was a big deal back then—now, it’s more of a sad story.

• Pomfret Town House: Built in 1841 and now lovingly cared for by the Pomfret Historical Society, this spot offers a glimpse into how things used to run around here.

• Christ Church: If stained glass is your thing, this church has windows designed by none other than Louis Comfort Tiffany.

• Old Pomfret Town House: Located on Town House Road, this 1841 building is another well-preserved piece of Pomfret’s past.

• Former Pomfret Congregational Church: This church stood proudly on Pomfret Hill until a fire tragically destroyed it in 2013.

Pomfret is also full of homes dating back to the 17th and 18th centuries, which really lock in that historic charm.

Shopping in Pomfret CT

Now, if shopping’s more your speed, Pomfret’s got some CT hidden gems for you to explore. It’s all about small-town charm here, and the shops reflect that perfectly.

• Pomfret Spirit Shoppe & Wine Shed: Wide selection of local and international wine, beer, and gift baskets—perfect for dinner or a thoughtful present.

• Old Wood Workshop: Handcrafted wooden goods, available by appointment only. A personalized shopping experience with one-of-a-kind pieces.

• Majilly: Unique gifts and eclectic items, great for finding something special to take home.

• Farmers Markets and Seasonal Events: Shop local produce, handmade goods, and antiques at farmers markets or town-wide yard sales—perfect for a little treasure hunting.

Restaurants in Pomfret CT

When it’s time to grab a bite, Pomfret’s got some delicious spots to choose from. Whether you’re in the mood for casual eats or a sit-down meal, here’s where you should go.

• The Vanilla Bean Café: Cozy spot in a restored 19th-century barn, serving soups, gourmet sandwiches, and fresh pastries. Known for live music and open-mic nights.

• We-Li-Kit Ice Cream: Farm-fresh ice cream with 16% butterfat and fun flavors like ‘Purple Cow’ and ‘Roadkill.’ Seasonal options keep things interesting at one of the best ice cream shops in CT.

• Frog Rock Summer Shack: Casual summer menu with live music and community events. Perfect for hanging out with friends in a laid-back atmosphere.

• The Inn at TONMAR: Charming New England inn offering locally sourced, seasonal dishes in a cozy, relaxed setting.

Directions to Pomfret CT from Greenwich, CT

So, you’re headed to Pomfret, huh? Well, you’ve got a couple of ways to get there depending on your mood—whether you’re up for a road trip or navigating the wild world of public transit.

Driving

• From Greenwich, CT: About 120 miles, roughly 2 hours and 15 minutes.

• From NYC: Just under 3 hours.

• Take I-95 North to I-395 North, then local roads into Pomfret. Easy drive with scenic spots along the way.

Public Transportation

• Step 1: Take Metro-North from Grand Central or Greenwich to New Haven.

• Step 2: Amtrak from New Haven to Hartford.

• Step 3: Taxi or rideshare from Hartford to Pomfret (no direct bus service).

Other Options

• Car rental: Convenient for flexibility.

• Ride-sharing: Possible but pricey for the distance.

Pomfret is about 40 miles from Hartford and 60 miles from Boston, accessible via U.S. Route 44 or scenic Route 169.

Hotels, Inns, and Places to Stay in Pomfret CT

Pomfret’s not exactly overflowing with hotels, but that’s part of its charm. What you will find are cozy, unique spots that give you a true taste of rural New England.

• The Gwyn Careg Inn: Historic 1810 Colonial Revival mansion with six suites and lush gardens. A beautifully restored historic inn with plenty of charm.

• Inn at Fox Hill Farm: Peaceful 1713 family farm on 75 acres along scenic Route 169. Stay in the cozy cottage on a bed and breakfast farm stay, enjoy lake views, and relax with breakfast and hammock time.

• Inn at TONMAR: Classic New England charm with stone walls, gardens, and hilltop views. Two room options (queen or twin beds), Wi-Fi, and a gourmet breakfast.

More Nearby Cities and Towns to Explore Near Pomfret CT

While you’re in the area, it’s worth checking out some nearby towns of Northeast Connecticut. Each has its own little charm, and they’re close enough for a quick day trip.

• Woodstock, CT: Just north of Pomfret, known for historic homes, scenic countryside, and the annual Woodstock Fair in late summer.

• Putnam, CT: Busy downtown with shops, restaurants, art galleries, and events like farmers markets and festivals.

• Brooklyn, CT: Small-town charm with local shops and a cozy vibe, perfect for a quiet afternoon.

• Thompson, CT: Ideal for nature lovers, offering parks, hiking trails, and scenic spots like Thompson Dam and Quaddick State Forest.

• Killingly, CT: Rich in history with modern amenities, including shopping and dining.

• Foster, RI: Great for outdoor activities, with plenty of hiking trails and open space just over the state line.

Tl;dr

So, whether you’re into history, nature, or just looking for a peaceful escape, Pomfret, CT, has you covered. It’s the kind of place where you can slow down, take in the scenery, and soak up that classic New England charm. From its rich history to its stunning landscapes, this little town offers a slice of life at a pace that feels just right. Come visit and see why Pomfret’s been a hidden gem for centuries—you might just find yourself wanting to stay awhile.

Frequently Asked Questions

Where is Pomfret located?

Pomfret is in Windham County, Connecticut, about 40 miles from Hartford, 60 miles from Boston, and around 30 miles from both Worcester, MA, and Providence, RI.

What is the population of Pomfret?

As of the 2020 census, Pomfret has about 4,200 residents—small, but cozy!

What are some notable attractions in Pomfret?

Pomfret has plenty to see and do, including:

• Mashamoquet Brook State Park

• Wolf Den State Park

• The Air Line Trail for hiking and biking

• Connecticut Audubon Center at Pomfret

• Scenic drives along Route 169

• Local wineries and distilleries for a taste of the region

What educational institutions are in Pomfret?

Pomfret offers:

• A Community School for Pre-K through 8th grade

• Two private boarding schools: The Rectory School (Pre-K–9) and The Pomfret School (9–12)

• Most high school students attend Woodstock Academy

What outdoor activities are available in Pomfret?

If you love the outdoors, Pomfret is perfect. You can enjoy:

• Walking, hiking, and mountain biking trails

• Horse trails for equestrian enthusiasts

• Birdwatching, especially in the area’s grassland habitats

• State parks for all kinds of outdoor adventures

What is Pomfret known for?

Pomfret is famous for its:

• Rural New England charm

• Historic homes from the 17th and 18th centuries

• Beautiful vistas and winding country roads

• A strong commitment to preserving open spaces and its small-town feel

Are there any annual events in Pomfret?

Yes, Pomfret hosts a few special events each year, like:

• The Memorial Day parade

• The Holiday Tree Lighting and Carol Sing on the Town Green in December

How old is the town of Pomfret?

Pomfret is one of Connecticut’s oldest towns, incorporated in June 1713. It celebrated its 300th anniversary in 2013!

What industries are present in Pomfret?

While Pomfret stays true to its rural roots, it does have a few industries, including:

• Hull Forest Products

• Loos & Company

• Fiber Optics Technology, Inc.

How is Pomfret governed?

Pomfret uses a classic New England system of town government with a three-member Board of Selectmen, a six-member Board of Finance, and Town Meetings for legislative decisions.