9 Outdoor Happy Hours for Cocktails in Westchester

From Katonah to White Plains, look no further for the booziest beer gardens and outdoor happy hours to while away your early evenings.

You know the old saying: “It’s not summer until someone takes a lawn dart to the face.” Or something like that; we’re sure you have your own variation. The point is, after all the shenanigans, the one true way to know the warm weather has arrived is to get out of work, throw your jacket aside, and knock back some refreshing adult beverages with your friends and coworkers in the crisp, cool air.

Yes, we’re talking outdoor happy hours. Westchester is filled with venues sporting decks, awnings, patios, and rooftop lounges. We thought we’d help give you a head start with a breakdown of some of our favorite alfresco locales for imbibing.

The Brazen Fox 

75 Mamaroneck Ave, White Plains; 914.358.5911  

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Visit this family-friendly restaurant located in downtown White Plains for drinks on the rooftop patio. Happy hour is Monday through Friday from 4–8 p.m. with food and drink specials included. You can also enjoy live music during the DJ Party Nights, which start at 11 p.m. During the outdoor happy hour, cocktails, draft beers, and wines are all $7. 

 

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Captain Lawrence Brewing Co.

369 Lexington Ave, Mount Kisco; 845.261.3279
444 Saw Mill River Rd, Elmsford; 914.741.2337

Stop by this brewing company for happy hour at one of the two 2024 Best of Westchester winner’s locations. The brewery happy hours run all day, with drinks until 10 p.m. on Wednesday (with a food special on wings from 4-9 p.m.), 4-6 p.m. on Thursday, and 2-6 p.m. on Friday. Also on Friday, take advantage of BOGO drinks from 12-7 p.m. Pair your $9 drafts, $31 pitchers, and $12 flights with a bite from the shared menu.

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Divino Cucina Italiana

524 Warburton Ave, Hastings-on-Hudson; 914.274.8501

Head over to this Italian eatery near the Hastings train station for a standout happy hour. Stop by the restaurant or speakeasy Tuesdays to Fridays from 4-7 p.m. for $8 house wines, $8 cocktails, $5 beers, and an array of appetizers.

Freebird Kitchen & Bar

161 Mamaroneck Ave, White Plains; 914.607.2476

“The only rooftop beer garden in White Plains” doesn’t disappoint. Look forward to views of the cityscape and clear blue skies this time of year. Stick around for the outdoor happy hour bar menu on Tuesdays to Thursdays from 3:30-6 p.m. and Fridays from 2-6 p.m., during which time you can enjoy drinks starting as low as $4.

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Freebird chicken sandwich
Chicken sandwich at freebird. Photo by Sabrina Sucato

Hudson Prime Steakhouse

5 N Buckhout St, Irvington; 914.231.6800 

This family-owned restaurant has exquisite Hudson River views, with a variety of select cuts and dry-aged meat. Happy hour is Tuesday to Friday from 4–7 p.m., during which time you can enjoy beers starting at $6, house wine and cocktails for $10, and plenty of happy hour bites.

Hudson Social

11 Station Plz, Dobbs Ferry; 914.478.3634

Soak in the Dobbs Ferry waterfront alongside a meal made with local ingredients and a cocktail at happy hour prices. On Monday to Friday from 3-6 p.m., select beers and all wines are $9, draft beers are $6, and cocktails and martinis are $10. If you’re looking for a $9 bite, you can choose from chicken wings, pretzel bites, cheese quesadilla, fried pickles, chicken tenders, or chips and guacamole.

Le Fontane

137 Somerstown Tpke, Katonah; 914.232.9619

If you’re trying to up your happy hour game, try Le Fontane. Fit with a garden and a bubbling fountain, this patio is the perfect summer setting for happy hour indulgences. Le Fontane’s happy hour runs 4-6:30 p.m. on Mondays and 12-6:30 p.m. on Tuesdays through Fridays. For sipping, choose between $5 and $8 wines, $5 appetizers, and $3 off any cocktail.

Southern Table Kitchen and Bar

39 Marble Ave, Pleasantville; 914.618.3355

Come to Southern Table for tasty, farm-fresh Southern cooking. Happy hour is Monday through Friday from 3–7 p.m. On Mondays, margaritas are half price, while Wednesdays are all about half-priced bottles of wine. Margaritas start at $16, while wine starts at $13. 

 

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The Tapp

17 N Broadway, Tarrytown; 914.229.3239 

This Westchester bar features Monday game nights, Tuesday trivia, Wine Down Wednesdays, and Thursday karaoke. Outdoor seating is also available. Come to happy hour from 4–6 p.m., during which time you can get $2 off draft beer, and glasses of wine or prosecco for $8. Appetizers are $6 to $8. 

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