These Are Our Favorite Westchester Wine Bars For Any Occasion

For day drinking, cocktail hour, date night, or pretty much any time.

Photo courtesy of Boro6

Boro6 Wine Bar

Encased in glass and set on a corner in downtown Hastings-on-Hudson, Boro6 features a regularly revolving by-the-glass pour list. Wines cover Old World and New, with a bump in rosé offerings come spring and summer. Pair your pours with plates of charcuterie, burrata with brown butter and sage, or wedges of toast piled with mushrooms.

Great For: A first date. Sit at the bar or tuck into one of the window-backed tables to share small plates and debate the merits of this Oregon Pinot Noir versus that French Bordeaux.

Where: 549 Warburton Ave, Hastings-on-Hudson; 914.231.9200


The Red Pony

The Red Pony is the wine bar Westchester has been waiting for. Occupying a corner in downtown Rye, the bar is bright, modern, and fresh. Step inside, and the extensive wine list spans the conventional and the unexpected. There are a couple pages of glass pours for both reds and whites, with often-humorous descriptions. Vacillating between a Nebbiolo and a Pinot Noir? The knowledgeable staff can advise. While Red Pony isn’t inexpensive, it’s a great place to explore some unique varieties and traditional grapes from lesser-known regions. They even have multiples of sherry.

Great For: Geeking out and trying something new.

Where: 53 Purchase St, Rye; 914.481.4220


Ernie's Wine Bar + EATS

Ernie’s may be minute — nine seats cluster around a copper-topped bar; the rest of the space is filled with six two-tops, a farmhouse table for groups, and corner booth — but its glass-pour program is anything but small. More than 20 whites and two dozen reds are available by the glass, and owner Luisanna Scalera switches offerings up from time to time. The bar, which is across from the Bronxville train station, attracts the commuter crowd, making it a good place to hang or network. Location may not be the only reason commuters flock here: Ernie’s has possibly the friendliest bar team in the county.

Great For: Live music. Petite as it may be, Ernie’s hosts live music every Wednesday and Friday.

Where: 7 Pondfield Rd, Bronxville; 914.652.7859


Bar'Lees in Mamaroneck

Once upon a time, Bar’Lees had hundreds of wines on the glass-pour list, including a series of old and rare wines. Owner Colin Goundrey has since limited the list, feeling that his wine preservation system wasn’t standing up to his expectations for older vintages. (Perhaps he could have seen that coming had he availed himself of the tarot-card reader who appears here every Tuesday evening.) Today, Bar’Lees by-the-glass list still has a good selection of reds and whites, plus some rare wines from recent vintages. There’s also an extensive whiskey program.

Great For: An education. On the fourth Wednesday of the month, Bar’Lees hosts a wine-tasting meetup. Goundrey sets the theme, which alternates between single-varietal series and more obscure ideas (attendees bring a bottle to share). For $15 guests get many tastes as well as an array of small bites.

Where: 157 Mamaroneck Ave, Mamaroneck; 914.630.7512



Where else can you craft your own whiskey flight with over 125 choices? Where can you make a flight with rosé, red, and white wines? ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ WINE :wine_glass: FLIGHT Choose any 3 out of our 30 wines which includes a selection of 12 Reds, 3 Ports, 9 Whites, and 6 Sparkling. ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ WHISKEY :tumbler_glass: FLIGHT Choose any 3 out of our selection of 72 whiskeys which includes 24 Bourbon, 24 Rye, 9 Irish, 6 Japanese, 6 Canadian, and 3 Tennessee. ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ Or try one of our 24 “Whiskey Family Flights” which lets you taste 3 different whiskeys from your favorite distilleries! ⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀⠀ #Flightsbar #Wineflight #Whiskeyflight #Macallan #flights #westchester #hudsonvalley #pleasantville #winetasting #whiskeytasting

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Flights Bar

A block and a half off the main drag in Pleasantville, Flights oozes dark wood sophistication. As the name suggests, this bar is dedicated to taste testing. For $24, guests can choose three pours from a menu of 30 different reds, whites, bubbles, and ports. Plus, there’s an equally extensive whiskey list, including flights of Pappy Van Winkle.

Great For: A wine versus whiskey smackdown. While he samples a selection of red, white, and bubbles, she can compare between, say, Hudson Baby Bourbon, Jack Daniels, and a 12-year Japanese single malt.

Where: 10 Marble Ave, Pleasantville; 914.769.4040

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