A hamlet in the town of North Castle, Armonk boasts the corporate headquarters of IBM, Swiss Re, and MBIA, but don’t let that fool you. The town is also home to the kind of small-town living that makes people love Westchester, with high-fashion boutiques, historic charm, and local eateries.
11 a.m. Let breakfast bleed into lunch at The Beehive (30 Old Rte 22). While the menu does include healthier options, this is the time to ditch your diet and indulge in elevated diner classics, like challah French toast, plate-sized cinnamon buns, banana pancakes, waffles, and eggs with crispy hash browns.
12:30 p.m. Give your credit card a workout at Main Street’s boutiques. Browse sweaters, candles, weekender bags, and more, often from small, New York-based designers, at STILE: Fashion Home (428 Main St). Then, check out sleek Tru Grace (419 Main St) for downtown-cool looks from designers like Isabel Marant and Alexandre Birman.
1 p.m. Prep for your next ski trip at Hickory & Tweed (410 Main St). Open since 1961, the shop has everything you’ll need to hit the slopes — skis, apparel, and equipment — plus warm coats and cozy sweaters to keep you warm during the next bomb cyclone.
2:30 p.m. Turn down Bedford Road, toward Maple Avenue. This short stretch is the Bedford Road Historic District, with nine wood-frame buildings from the mid-1800s. At the end of the block, stop to appreciate St. Stephen’s Church (50 Bedford Rd). Built in 1842, the timber-lined Greek Revival building has been a community hub for more than 175 years, with the tombstones of 22 Civil War soldiers in its adjacent cemetery.
2:45 p.m. Backtrack to Tazza Café (400 Main St) and grab a chai latte, coffee, or hot chocolate with a jolt of espresso to go.
3:15 p.m. When the temperature drops below freezing, Wampus Pond (811 Rte 128) transforms into an ice-skating hotspot. Bring your own skates, and don’t worry about falling through the ice. The pond is inspected daily by Westchester County Parks. If the white flag with a green ball is flying, you’re safe to toe loop, lutz, and axel to your heart’s content.
4 p.m. Pray that Beascakes (575 Main St) hasn’t sold out of chocolate chip cookies. Full of melting chocolate wafers, they’re worthy of their own trip to Armonk. After, pop into Wine Geeks (559 Main St), a gas station-turned-wine shop. Its $15-and-under table, representing a wide array of varietals, is one of the truly great deals in this part of the county.
4:45 p.m. Back in town, hit LUXE Luxury Labels (41 Maple Ave) before it closes. The high-end consignment shop is the place to score a deal on Chanel, Dior, Valentino, Jimmy Choo, YSL, and more.
5:30 p.m. You’re at Fortina (17 Maple Ave) just before the end of happy hour. Grab a couple seats at the wide stone bar to take advantage of deals on drinks, chicken-parm sliders, garlic knots, and select pizzas. Some mozzarella sticks wouldn’t hurt either.