The Best Bar Crawl in Westchester

If you thought we’d say White Plains is the best neighborhood for a bar crawl, with its bevy of carbon-copied bars lining Mamaroneck Avenue, you’d be completely wrong. Tarrytown and Sleepy Hollow take that distinction. Picturesque but humming with activity, the streets of these two towns are lined with watering holes for every kind of imbiber. Extreme walkability plus a view plus tasty cocktails? Don’t mind if we do (and we did). We started our night at Bridge View Tavern. While its titular view has been partially blocked by new construction, this friendly bar and grill, tucked along a side street, offered well-crafted flights of beer—with brews including Allagash Tripel Ale, Franziskaner Hefe-Weisse, and Sixpoint Sehr Crisp Pilsner—and enough sports on TV to satisfy all types (they even switched to a soccer game later in the night for us). After finishing our flights, we went up the street to The Huddle, a friendly little dive if we’ve ever seen one, offering just the right amount of charm. It’s the sort of place to let loose (we’re pretty sure you can waltz in dressed in pajamas and no one would be put off). We’re not 100-percent sure if our server was an actual bartender or just a regular, but we honestly didn’t care—we were too deep into Cupcake Wars on the TV. After we watched our fair share of the Food Network, we took a short ride to Tarrytown. We hit a few places before landing at The Tapp—our personal favorite in the area—which hosted a younger crowd at its long bar and handful of tables. With a lengthy list of local beers on tap (or Tapp?), like Yonkers Lager and Victory Donnybrook Stout, and a thin-crust pizza from heaven, this was a perfect place to end the night. But then, it wouldn’t be very much of a bar crawl, would it? Walking past Little B’s, we weren’t sure if it was even a bar, but after peering in the window and seeing a number of taps, we took the plunge. Little B’s, which is open ’til 2 am, hits the spot after a long night of drinking. Part diner, part bar, it has a build-your-own burger menu to stop your heart. Most of the patrons—a mix of young and old—were downing burgers, fries, and wings. We kept it simple, however, with more beer and a tasty Coke float. We then topped off at the more-restaurant-than-bar Sweet Grass Grill. It may not have the most impressive or extensive cocktail list, but if you’re looking for a well-made drink with locally distilled spirits, it’s the perfect place for a nightcap. That’s five top-notch choices for your bar crawl. So if you don’t find something that tickles your fancy here, apparently drinking isn’t your thing. 

Our Westchester Home Design Awards event is June 26!

Our Wine & Food Festival returns June 4-9!

Our Wunderkinds event takes place on May 23!

Our Best of Business Ballot is open through May 15!

Our Healthcare Heroes Awards event takes place on May 9!

Our Westchester Home Builders Awards take place on April 4!

Our Diversity, Equity & Inclusion Forum is March 14!

Unveiled: A Boutique Bridal Brunch is February 25!

Our Best of Westchester Elimination Ballot is open through March 6!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.