A season near Pawling follows the calendar. June brings the Saturday market to the village green, September turns to pumpkins at Dykeman Farm, and the vineyards stay open through the winter. These are the markets, wineries, and shops we send people to.
Farmers Markets and Farm Stands
The Pawling Farmers Market runs Saturdays from 9am to 1pm on the Pawling Village Green, from mid-June through the end of September. The 2026 season ran June 13 to September 26, so it has wrapped for the year and returns in June. Look for fruits, vegetables, cheeses, and baked goods from regional growers, plus crafts such as jewelry, soaps, photographs, and paintings.
Once the market ends, the farm stores carry on. Dykeman Farm in Pawling has a farm stand open seven days a week, 10am to 5pm, from July 1 through October 31, about twelve minutes from the farmhouse. Fishkill Farms in Hopewell Junction sells organic vegetables and eco-certified fruit year-round. Harvest Moon Farm and Orchard in North Salem opens its farm store daily from 9am to 6pm, April through Christmas, with eggs, vegetables, 100 percent grass-fed beef, pasture-raised turkeys, and apple cider donuts made fresh every day. Our guide to Apple Picking and Orchards Near Pawling has the details on all three.
Crown Maple at Madava Farms in Dover Plains is a maple syrup estate about 20 minutes from the farmhouse. The Patterson Flea Market at 3165 Route 22 in Patterson is open Sundays from 8am to 3pm.
Good to know: Hours change with the season, so confirm with each farm before you go.
Vineyards and Wine
Millbrook Vineyards & Winery is a 130-acre property in Millbrook with a 30-acre vineyard and walking trails, about 40 minutes from the farmhouse. It is open year-round, Monday through Thursday 12pm to 5pm and Friday through Sunday 12pm to 6pm. Walk-ins are welcome, groups of six or more should call ahead at 845-677-8383, and individual tastings can be booked online. Food trucks park at the winery on weekends from May through October.
There are three tastings. The Bar Tasting is $22 per person for five wines. The Overlook Tasting is $30 per person, seated indoors with vineyard views, starting with a Brut Rosé and followed by five wines, with optional small bites. The Overlook Terrace Tasting is $40 per person, outdoors with the same wines and terrace views. The lineup includes Tocai Friulano, Chardonnay, Pinot Noir, and Cabernet Franc.
Cascade Mountain Winery, at 835 Cascade Road in Amenia, is open year-round and roughly 19 miles from Pawling. Call 845-373-9021 for hours.
Good to know: Tasting prices are current as of this writing. Confirm before you visit.
Local Shops in Pawling
The village of Pawling is a short walk from the Metro North station, with shops along Main Street, Broad Street, and Charles Colman Boulevard.
Start with the bakeries. Sunflour Bakery & Cafe is at 5 Broad Street, a short walk from the train station and the Main Street shops. McKinney & Doyle bakes muffins, Danish, and cobblers. Pawling Bread Co is at 10 E Main Street.
Pawling Book Cove is the village bookstore, and Pawling Antiques at Old Dutcher House, a multi-dealer antiques shop, is inside it. Imperial Castle Toy Shop carries vintage and modern toys. Good Tidings Gift Shop is a boutique gift shop, and The Blue Olive is an olive oil and vinegar tasting room with gifts. Parrino’s Florist does flowers and plants, and Wineology Fine Wine & Spirits is the wine and spirits shop.
Just outside the village, in Patterson, Anglers’ Den is a full-service fly shop on Route 311.
Good to know: Hours vary by shop, so check before you go.