Water cascades through a rocky gorge at Bash Bish Falls, one of the Taconic Mountains’ most iconic destinations, set on the border between Massachusetts and New York. Photo: Escape Brooklyn

EB’s Top 5 in Hillsdale:

• Kayaking on Copake Lake: Spend an entire day on the water by renting a kayak or paddleboard through Copake Lake Boat & Ski. Rentals are available by the hour or for the entire day, starting at $25/hr.

• Flights at Roe Jan Brewing Co.: For an afternoon of beer tasting, build a flight of four beers to enjoy on the brewpub’s back deck. Keep it light and fresh with the Pill Hill (American Pilsner), 22.5 (Juicy IPA), Harlem Valley (Kolsch), and Roeliff (Saison Ale).

• Cross-State Hiking in Taconic State Park: In just under two miles, hike from New York into Massachusetts on the Bash Bish Falls Trail. The New York trailhead provides a more level path than the Massachusetts entrance, so park at the Bash Bish Lower Lot for a gentler start to the hike.

• Brunch at Little Cat Lodge: While dinners at Little Cat Lodge impress, the brunch menu is equally noteworthy. Start with a mimosa, then dig into the Little Cat Benedict, which swaps the traditional English muffins with potato latkes.

• A Day Trip to Hudson, NY: Just half an hour from Hillsdale, the thriving town of Hudson offers a more bustling environment. Check out the Escape Brooklyn Guide to Hudson to inspire this worthwhile day trip.

Tucked where the Hudson Valley meets the Berkshires, Hillsdale and the neighboring town of Copake offer a rural retreat shaped by mountain air, wooded trails, and a quietly evolving food scene. Surrounded by protected parkland and dotted with lakes, farms, and small hamlets, this corner of Upstate NY feels both peaceful and purposeful – an ideal setting for long hikes, outings on the lake, and post-adventure libations.

In summer, quiet trails lead to ridgelines and waterfalls, while Copake Lake offers a calm spot for swimming, paddling, or simply drifting dockside. Come winter, nearby Catamount Mountain Resort becomes the main draw, with ski trails and lodge-style dining that anchor the cold-weather season. Year-round, the towns’ compact centers provide a thoughtful mix of cafés, breweries, and restaurants, each one adding a layer to the area’s low-key appeal.

Read on for our Hillsdale and Copake guide – including where to hike, ski, eat, and unwind in this scenic stretch of New York.

What to Do in Hillsdale, NY: Exploring the Outdoors

Start the morning with a stop at Twisted Sisters Coffee House in the center of town, before heading into the mountains. Just over the Massachusetts border, the Bash Bish Falls Trail offers a short, scenic hike to a dramatic waterfall. For more elevation gain, the Cedar Brook Trail in Taconic State Park climbs along its namesake stream before linking with the lengthy South Taconic Trail for broader access to the ridgeline. On Saturdays from May through November, the nearby Copake Hillsdale Farmers Market brings together local farms, small-batch foods, and handcrafted goods on the Roe Jan Park grounds.

During summer, Copake Lake draws paddlers and boaters to its calm waters. Kayaks, paddleboards, and pontoon boats are available for rent by the hour or day through Copake Lake Boat & Ski. In winter, Catamount Mountain Resort straddles the New York-Massachusetts border and offers 43 trails across 1,000 feet of vertical, with terrain suited to beginners and experienced skiers alike.

Where to Eat + Drink: The Best Bars and Restaurants in Hillsdale, NY

Dine fireside at Little Cat Lodge, and watch skiers descend Catamount Mountain in the distance. Photo: Julian Bracero

Twisted Sisters Coffee House offers a cozy start to the day, with hot coffee and hearty breakfast sandwiches served in the heart of town. Nearby, Crook & Larder pairs well-sourced coffee with fresh pastries in the morning, and rotates a selection of prepared salads and sandwiches for an easy midday option.

Later in the day, Roe Jan Brewing Co. opens its doors early on weekends, serving house-brewed beers alongside a menu of comfort-driven pub fare in a restored historic building. For dinner, Little Cat Lodge’s Alpine-style restaurant sits at the base of Catamount Mountain, blending rustic lodge design with mid-century elements. The seasonal menu focuses on regional ingredients and well-balanced dishes, offering a welcoming setting whether after a day on the slopes or a summer evening outdoors.