VISIT CHATHAM, NY

The picturesque Village of Chatham, New York is nestled between the Hudson River and the Taconic Mountains in beautiful Columbia County. With views of rolling farmland and a quaint main street lined with historic buildings, the town is well worth exploring after the Fair. Don’t miss Chatham’s downtown, which is dotted art galleries, restaurants, a record shop, and cultural venues.

ROAD TRIP

If you’re traveling to the Fair, don’t be discouraged by the drive—it’s part of the experience! The scenic Taconic Parkway winds north through wooded hills and farmland with breathtaking views of fall foliage. Here are some shops and sights to check out along the drive.

From New York City – Consider stopping off in the lower Hudson for wine-tasting at Fjord Vineyards or Benmarl Winery. Benmarl is hosting their annual Grape Stomping Festival the same weekend as TAF. Beacon, Rhinebeck, and Hudson are short diversions from the route. Only twenty minutes from Chatham, Hudson has many antique stores, galleries, and restaurants to explore.

From Connecticut – On your way, visit Millerton or Millbrook, New York for more galleries, restaurants, and historic small-town vibes. Millbrook Vineyards offers a great selection of Hudson Valley wines and we like Canoe Hill in Millbrook for cocktails or dinner.

From Boston – Stop off in Great Barrington or Lee, Massachusetts for more leaf-peeping, culinary scenes, and antiquing. Knollwood Antiques is a multi-vendor antiques and decor gallery in Lee. In Great Barrington, The Berkshire Galleries is packed with quality antiques and Prairie Whale is the place to make a reservation. Hancock Shaker Village and Historic Deerfield are a stone’s throw away.