Things To Do In Pound Ridge NY: Top 15 Most Unique Spots | Stanton House Inn

 

A fall day along the trails of New York's Pound Ridge

Pound Ridge NY is a charming town nestled in the picturesque hills of Westchester County. It’s located about 50 miles outside of Manhattan, or, as the locals say, 50 miles and 50 years away from the hustle and bustle of the Big Apple. Not having a train station in-town has preserved much of it’s small town New England historic character. It still offers a delightful blend of history, natural beauty, and modern conveniences. Pound Ridge is a great place to visit for a day or weekend. There are lots of outdoor activities, historical sites, art, and delicious food.

Ready to discover the best things to do in Pound Ridge NY? Let’s get into it:

Quick hits

  • Explore the stunning natural beauty of Pound Ridge, NY and all its outdoor activities!
  • Experience a unique round of golf at the scenic Pound Ridge Golf Club or explore local art galleries & studios.
  • Enjoy family fun with parks, playgrounds & events like Farmers Markets and Concert Series, plus hotels to stay in nearby towns!

 

A Brief History of Pound Ridge, NY

Accomplished regional artists congregate in this artsy corner of Westchester County for the freedom of solitude

Pound Ridge, a picturesque town in Westchester County, New York, has a rich history dating back to the early American settlement period. Its development was influenced by Native American and European influences. Originally known as Basket Town, it was a leading maker of straw oyster baskets for Long Island Sound fishermen. Founded in 1788, Pound Ridge remains off-the-grid and self-sufficient, with no traffic lights. The town’s unique blend of Native American and European influences has made it a unique and charming community.

 

Native American Period

Pound Ridge gets its name from the area’s original residents. Locals kept a pound on the territory where they kept game on the hoof until they needed it for food. Local Native Americans in the early 17th century were part of the Wappinger Confederacy. The tribes were part of the Kitchawong, Siwanoy, and Tankiteke bands. The Wappinger Confederacy joined Kieft’s War in 1640. Tensions over land use between New Netherland and nearby Native American tribes led to hostilities. In 1644, those tensions erupted into the Pound Ridge Massacre. A village on the site of present-day Pound Ridge was attacked by 130 New Netherland soldiers. The attack killed between 500 and 700 Indians, including 25 Wappinger tribe members. The Dutch, meanwhile, lost only one man. The area was first settled by Europeans in 1718 in the present-day Long Ridge Road area. Most original settlers were from Stamford, Connecticut.

 

Colonial Era

Wooded trails in winter, situated in the north of Westchester County

The Pound Ridge area was part of the Cortlandt Manor grant. The grant covered over 86,000 acres from the Hudson River to the Connecticut border. The manor itself was in Croton-on-Hudson, NY. The Lockwood family first purchased land in 1737, followed by the Scofield family in 1745 and the first Fancher in 1758. The term “Old Pound Ridge” was first recorded in North Castle records from 1737 and Stamford records in 1750. In the 1700s, the Boutonville area of Pound Ridge was the center of a 50-year land dispute. After a legal battle, clear title to the 3,000 acres was given to the Van Cortlandt heirs in 1788. The farmland in Pound Ridge and Lewisboro sections was part of the Van Cortlandt Manor lands, divided into “great lots” of about 3,000 acres each.

 

Revolutionary War

During the American Revolutionary War, Pound Ridge was the site of a battle. 300 American rebels were attacked by 200 British soldiers led by Banastre Tarleton. The attack was planned to draw Washington’s army away from the Hudson River. Tarleton’s troops took an indirect northern path to Pound Ridge. They burned the Presbyterian Church and Major Lockwood’s house. Then, they left with prisoners, cattle, weapons, equipment, and the battle flag. Reports on battle casualties are contradictory.

 

1800s

Pound Ridge, incorporated in 1788, was an agricultural community with a population of 1,062 by 1790 and 1,256 by 1800. The town was a center for shoemaking, basketmaking, and the oyster industry. That said, the cottage industry style of shoemaking declined as it employed more full-time workers in factories. Pound Ridge provided 109 men to fight in the American Civil War. In 1869, the Stamford Water Company constructed Trinity Lake, which hosted annual farmers’ picnics.

 

1900s to Today

Pound Ridge experienced a population decline from 1,417 in 1860 to 515 in 1920, as dairy farming replaced general farming. The town lost all three post offices by 1903, and in 1911, a series of fires burned hundreds of acres. In 1925, Westchester County bought land in Pound Ridge and Lewisboro. They made it the Pound Ridge Reservation, but later changed the name to Ward-Pound Ridge Reservation in 1938. The Reservation had a Civilian Conservation Corp camp from 1933 to 1940. The camp improved roads, planted trees, built bridges, shelters, and a museum.

 

Richard Gere, Mike Myers, and Susan Sarandon have all lived in Pound Ridge. They were attracted to the privacy and peacefulness of the large properties. The New York Times recently pierced the veil of that privacy, though the area remains remote.

Top Things to do in Pound Ridge, NY

Pound Ridge is not as well-known as nearby commuter towns like Bedford, NY, and Mount Kisco because it lacks a train station. The houses in the area are spread out over the hillsides and valleys. They are a mix of old and new, with white-painted antique farmhouses and modern homes. The landscape is steep and rocky, shaped by glaciers. It’s a little more country and artsy here. It continues to have the same rural New England feel that it’s had for centuries.

 

The Pound Ridge Land Conservancy manages 19 nature preserves in the 23-square-mile town. Seven of these preserves have wooded trails, making hiking a great way to explore.

 

Ward Pound Ridge Reservation

Cross-country skiing through the wooded trails of Ward Pound Ridge Reservation

Ward Pound Ridge Reservation is Westchester County’s largest park. It covers 4,315 acres and has activities all year. There are lean-to camping areas, as well as fishing and cross-country skiing areas and picnic areas.

 

When you walk on the wooded trails at Ward Pound Ridge Reservation, you are likely to see something wild in this Biodiversity Reserve Area. The park has open spaces like meadows, wet meadows, sandy moraines, and vernal ponds. It also has rustic woodlands with evergreen plantations, oak, hickory, and maple forests, and wooded wetlands. The park is traversed by two streams, Cross River and Stone Hill River, which are home to thirteen species of native and stocked fish. This massive park offers some of the best upstate NY hikes so close to New York City.

 

The reservation was originally part of Cortlandt Manor and was settled by Connecticut farmers. The county bought the property in 1938. They changed the name to “Pound Ridge” and added “Ward” to honor William Lukens Ward. He was Westchester’s county leader from 1896 to 1933.

 

Enjoying a little peace while fishing in July at Ward Pound Ridge Reservation

The Works Progress Administration Gallery at Ward Pound Ridge Reservation

The Gallery is in the park’s administrative building. It shows art by established, emerging, local, and regional artists all year. The W.P.A. Gallery shows different art like paintings, photos, and other works.

Trailside Nature Museum at Ward Pound Ridge Reservation

The Trailside Nature Museum at Ward Pound Ridge Reservation is an educational place for all visitors. The museum displays nature and the reservation’s history with permanent and seasonal exhibits.

 

The museum also offers weekend nature interpretive programs throughout the year. They’re a unique opportunity to learn about and appreciate the local flora and fauna.

 

Tee Off at Pound Ridge Golf Club

Playing golf at the Pound Ridge Golf Club, a Pete Dye design

Pound Ridge Golf Club is an 18-hole public facility and a Pete Dye design, one of the most well-known golf course designers.

 

Golf enthusiasts will feel right at home at the picturesque Pound Ridge Golf Club. This 18-hole championship golf course features:

  • Rolling hills
  • Elevation changes
  • And stunning views of the countryside

The club has a driving range, practice green, a fully stocked pro shop, and a full-service restaurant, so you can have a well-rounded golf experience.

 

The 17th hole is famous for its downhill shot and bunkers around the green, making this one of the most memorable public golf courses in the area.

Art Galleries and Studios in Pound Ridge, New York

Discover the work of local artists and artisans at art galleries and studios such as:

 

These venues provide a platform for accomplished regional artists to showcase their creations. You’re sure to appreciate the artistic diversity and skill present in the Pound Ridge community.

 

Visitors can explore the galleries and studios to find unique pieces of art, and handmade crafts.

Cultural Events and Festivals

Celebrate the arts and creativity at cultural events and festivals in Pound Ridge at the Pound Ridge Harvest Festival.

 

It’s an opportunity to experience artistic performances, exhibitions, and workshops. There’s no question the town’s committed to fostering a vibrant arts scene.

 

Some family-friendly events to attend include:

 

Food Truck Fridays, a foodie event that began in 2018 and takes place one Friday a month from May to September in Scotts Corners. Food Truck Fridays are an opportunity to get out and let the children run around. That’s the whole point, to create a sense of community in what is a spread-out town.

Shopping in Pound Ridge, NY

Classic car in the commercial district of Scotts Corners

Pound Ridge is an artisanal town. As such, it is home to a variety of shops and eateries, including vintage treasures, chic home goods shops, and unique boutiques. The tiny commercial district also features cheese shops, wine merchants, and florists. The town’s commercial center, Scotts Corners, is on Westchester Avenue. And it arguably is more robust than the downtowns in neighboring Bedford, NY, and Lewisboro, NY. It contains a supermarket, gas station, hardware store, dry cleaner, bar, and Italian restaurant. Literally, one of each.

 

Scotts Corners has seen a shift from antique shops to hipper businesses. Spots like The Kitchen Table and Booksy Galore have joined the fray in recent years. The charming boutiques, specialty shops, and dining establishments in the commercial district make it a delightful destination.

 

Restaurants in Pound Ridge, New York

Fine dining at the Inn at Pound Ridge

Pound Ridge boasts a diverse culinary scene, offering a variety of dining experiences for all tastes. From local favorites to farm-to-table establishments and sweet treats, the town’s restaurants are sure to impress.

 

Unearth the mouthwatering culinary options that Pound Ridge has to offer.

 

Inn at Pound Ridge

The Inn at Pound Ridge is a restaurant opened by French chef Jean-Georges Vongerichten. It exemplifies the sophistication of nearby big cities, tucked away on country roads. Few big-name New York City chefs have stayed in the area as long as Jean-Georges Vongerichten, who opened the Inn at Pound Ridge in 2014. The restaurant’s dining room is rustic and elegant with exposed wood ceilings and four working fireplaces. It is a favorite among ritzy northern Westchester residents. Vongerichten’s new restaurant has a different look from his typical high-end urbanism. And yet the food is still comforting and delicious. You can try ginger-marinated tuna tartare, black truffle and fontina pizza, or steamed black sea bass with orange and cumin.

 

Hotels, Inns, and Places to Stay near Pound Ridge, NY

Grace Farms, just over the border in New Canaan, of Fairfield County

Looking to make the trip up to Pound Ridge? This upper Westchester County hamlet is only a 30-minute drive our bed and breakfast in Greenwich, Connecticut. Other places to stay near Pound Ridge include:

 

A historic property in Bedford, New York, Bedford Post Inn features an eight-room luxury inn, a yoga studio, and two restaurants. Restored in 2007, it offers five room layouts, working fireplaces, and a terrace for practicing what you learned in the yoga studio. And yes, Richard Gere still owns it.

 

The West Lane Inn in Ridgefield, Connecticut, is a charming 1849 boutique hotel. The inn, which is located in the town’s first Cultural District, has 17 tastefully decorated rooms with private bathrooms. Guests here enjoy continental breakfast daily and yoga classes on the lawn of this Connecticut yoga retreat. The inn is also located in the town’s cultural district, making it convenient to various attractions.

 

Since 1925, the Roger Sherman Inn, is a historic restaurant and inn in New Canaan, Connecticut, has been a favorite for fine dining. The restaurant, housed in an 18th-century mansion, serves a mix of French and American cuisine, with rotating menu items throughout the year. With a lengthy wine list and mixed drinks, it’s ideal for special occasions or simply enjoying a little fine dining.

 

Frankly, any of the best hotels in Greenwich, CT, are convenient to Pound Ridge.

 

Directions to Pound Ridge, NY

Downtown New Canaan

Today, the town is still small and remote—exactly what its residents want to keep and why they choose it as a great place to live. Metro-North Railway stations are located in:

 

 

 

The drive from Pound Ridge to any of the stations takes about 20 minutes, and the train ride takes about an hour and ten minutes for a MetroNorth day trip.

 

And the drive from Pound Ridge to Midtown Manhattan via Interstate-684 takes just over an hour.

 

More Towns and Cities to Explore Near Pound Ridge, NY

Visit nearby towns and cities such as Stamford, Greenwich, and White Plains, NY, to broaden your exploration beyond Pound Ridge. Every place has its own things to do and see, so you can learn about the area’s history, nature, and culture. And unlike Pound Ridge, they’re much easier train trips from NYC.

Tl;dr

Pound Ridge, New York is a captivating place with a rich history, beautiful nature, and modern conveniences. Visitors of all ages will have a memorable experience in this charming town. It has a rich history, vibrant art scene, and diverse dining options.

Frequently Asked Questions

What is Pound Ridge known for?

Pound Ridge is a beautiful rural town treasured for its rolling hills and scenic country roads. Its hamlet, Scotts Corners, features various dining options and quaint boutiques, making it a great getaway spot.

Is Pound Ridge NY A good place to live?

Pound Ridge is an ideal place to live for those who seek a comfortable lifestyle, an outdoor-friendly atmosphere and rural feel. With parks, low noise levels, and its close proximity to New York City, Pound Ridge is an excellent place to live.

Is Pound Ridge expensive?

Pound Ridge is an expensive town, with a median listing home price of $1.3M and the cost for a family of four to live there estimated at $17,759 a month. It also has a median listing home price per square foot of $356, along with a median home sold price of $1.1M.

What outdoor activities are available in Pound Ridge, NY?

Pound Ridge is a great place to enjoy nature. You can hike, do winter sports, and learn at the Trailside Nature Museum. Hiking is a great way to get out and explore the area, with trails ranging from easy to difficult. In winter, people enjoy cross-country skiing and snowshoeing. The Trailside Nature Museum has educational programs for all ages.

What kind of dining experiences can I expect in Pound Ridge, NY?

Discover Pound Ridge’s best food by trying local favorites, farm-to-table meals, and delicious bakery treats.

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