Pawling Is a Small Town With Charm in Southern Dutchess County

Pawling may be small, but it packs a mighty assortment of restaurants and shops, not to mention a thriving arts community.

A southern Dutchess town with a charming village and plenty of open space, Pawling offers a quiet life surrounded by natural beauty. In an effort to retain the rural feel that is very important to its 8,000 residents, the town government is working to keep Pawling’s country qualities while still welcoming visitors and new arrivals to the area.

“We’re a small town; when you sit on your front porch, it’s quiet, there’s no noise or light pollution. We’re not looking to be overrun with development,” says Town Supervisor James Schmitt, who is working on local legislation to protect Pawling’s untouched land.

That land was settled by Quakers in the mid-1700s, but the area didn’t see many visitors until the construction of the New York and Harlem Railroad in 1848. One of the prominent hotels constructed during the era, the Dutcher House, still stands downtown on Oak Street—it now functions as an apartment building with storefronts on the first level.

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The Culture

Although small, Pawling has a thriving arts community. You can wander around two independent galleries, LAND Gallery and Live 4 Art Gallery. Popular venue Daryl’s House (owned by musician Daryl Hall, formerly of Hall & Oates) hosts musical artists and cover bands every week. Throughout the year, you can also catch classical and jazz performances at the nearby private school, Trinity-Pawling, as part of the Pawling Concert Series. The first show of the 2023-24 season features musicians John Pizzarelli and Jessica Molasky on October 13.

Small shops and restaurants line the streets of Pawling’s village. Above, storefronts on Charles Colman Boulevard.
Small shops and restaurants line the streets of Pawling’s village. Above, storefronts on Charles Colman Boulevard. Photo courtesy of Dutchess Tourism.

Pawling is known for its involved community that hosts several popular, annual events. “The town is very active, and we’re constantly doing functions to attract people,” says Schmitt. Coming up next is the annual community-wide yard sale on September 9: village streets are closed off to allow businesses and vendor booths to sell a variety of goods—residents can also participate by hosting sales at their own homes. Other events include the annual car show and the “unofficial” shortest Saint Paddy’s Day Parade in February—its route is only 223 feet long.

Family Life

If you’re considering moving to the area, keep in mind that the housing market isn’t as competitive as other nearby destinations. At press time, there were 21 single-family homes on the market with a median sale price of $642,500, according to Mid-Hudson MLS. Despite being in the country, Pawling is easily accessible via Metro-North (Harlem Line) and its proximity to I-84, which is 15 minutes away by car.

Most children attend schools in the Pawling Central District, which has an A- rating on niche.com. The town is also home to the Trinity-Pawling School, a 116-year-old boarding and day school for 7th- through 12th-grade boys.

On the Town

Pawling’s two-square-mile village is home to a variety of local businesses. “To me, it’s like the smaller scale version of other popular Hudson Valley towns. We don’t get the same amount of tourism, but we have some nice little restaurants and shops,” says Nicól Furlong, owner of NicólJoë NY Boutique.

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Looking to grab a bite? Head to McKinney & Doyle, a restaurant and bakery serving elevated American fare and fresh pastries; Tacos and Cones serves an array of inventive tacos and ice creams; you’ll find burgers and bar food at traditional Irish pub O’Connor’s Public House; La Guadalupana Mini Market II is a Mexican deli; and Dancing Bear Café, Sunflour Bakery, and Pawling Coffee Roaster all offer sandwiches, drinks, and baked goods for breakfast and lunch.

Great spots to go shopping include The Blue Olive, a specialty olive oil, vinegar, and gourmet salt store; the Yarn & Craft Box; the Book Cove; Pawling Antiques; and NicólJoë NY Boutique for men’s and women’s clothing. Every Saturday until October 7, you can also visit the Pawling Farmers Market from 9 a.m.–1 p.m. at the Pawling Village Green on Charles Colman Boulevard.

Immerse yourself in nature on The Appalachian Trail, which winds through the northern part of the town, and even has its own Metro-North station for easy access. Hit the trails at the Pawling Nature Reserve and be rewarded with vistas of the Harlem Valley. Visit Lakeside Park near the village for watersports and picnic areas.

Furlong, who moved to Pawling 20 years ago and has since brought up five children in the area with her husband, recommends the town to others in search of country living. “It’s definitely quieter and not for everyone, but if you’re looking for a wonderful place in New York to raise a family, this is it.”

To find a real estate agent in Pawling or any Hudson Valley town check out near-me.hvmag.com/realtors.

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Related: These Are the Most Affordable Towns in the Hudson Valley

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