7 Peekskill Happy Hours to Nurse Your Workday Wounds

After a long hard day at the office, unwind with these budget-friendly food and drink options.

Commute kick your butt? Boss got your down? Did that big presentation not go the way you wanted? Friend, you look like you could use a good happy hour.

Luckily for you, we just got done rounding up our favorite happy hours to hit in Peekskill and this northern Westchester foodie Mecca is the perfect place to grab some uplifting spirits and soul-saving nibbles so good you’ll be back in the office tomorrow bright-eyed and bushy-tailed!

Birdsall House

970 Main St

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First alphabetically, first in our hearts: Happy hour at Birdsall never disappoints whether you’re indoors or enjoying the outdoor beer garden picnic tables during warmer months. Running Monday through Friday from noon all the way until 7 p.m., specials include $5 draughts from the brew hall’s extensive rotating beer menu.

For snacks and nibbles, the smoked BBQ wings with house-made sauce are some of the best around, especially when paired with a side of fries with secret recipe ketchup and malt vinegar mayo. More adventurous options even include grilled lamb sliders, calamari salad, and shrimp quesadillas.


55 Hudson Ave

With more than 130 whiskeys on hand — the vast bulk of them New York locals — this more adult half of Taco Dive Bar is a tiny slice of heaven garnishing the rim of our lowball glass. Happy hour runs from 5 p.m. to 7 p.m. Wednesday through Friday and features half-price on all draught beers, as well as the half-priced “shot of the day.” (Big fans.)

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Pair it with any of their regular menu items — we suggest the tater tot nachos — for an after-work wind-down that’s top shelf.

The Eagle Saloon

21 S Division St

Another Hudson Hospitality Group establishment, this night spot is all about southern rock, good booze, and finger-lickin’ food. Monday through Thursday from 5 p.m. to 6:30 p.m. score any draught or bottled beer as well as cider and wine by the glass for half-price, along with discounted well drinks.

For food, we recommend taking all the cash you just saved and going in on some dry rub jumbo chicken wings, Eagle Nachos Supreme (oh my), or a hearty short rib quesadilla.

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911 South St

This South Street staple holds happy hour at the bar from 4 p.m. to 7 p.m. every Tuesday through Friday. Gleason’s has always been a place to grab a good drink, and you can grab any draught beer for just $5 if you show up at the right time.

Oenophiles and spirit drinkers won’t be left out: you get $1 off all wine, well drinks, and cocktails too. Regulars will also gladly tell you that Gleason’s isn’t a place to just snack on beer nuts, their house-made pizzas are insanely good. Happy hour guests can score one for just $5 at the bar.

Iron Vine

992 Main St

Peekskill’s happenin’ tapas bar gets and keeps its rep for a reason: Happy hour runs 5 p.m. to 7 p.m. on weeknights and includes — deep breath — $2 off tapas; $3 bottled beer; $5 draught beer; $6 house wine; $8 margaritas, mules, sangria, and mojitos; $9 Chandon, and $10 “bartender special” cocktails, rotated monthly.

Happy hour deals can only be had at the bar but if that’s not enough for you, you can always combine them with Iron Vine’s daily deals: Margarita Mondays ($6 plain, $7 flavored, specialty $8-10), Two-for-One Tuesdays (beer only), half-priced bottles for Wine Wednesdays, and Thirsty Thursdays, when every cocktail is just $10. There’s also Sangria Sundays with $25 pitchers, but we recommend saving that for an add-on to your bottomless mimosa brunch!

The Peekskill Brewery

47 S Water St

How could we round up the city’s best happy hours and not include its namesake brewery? Every weekday from 4 p.m. to 6 p.m. patrons can enjoy $2 off a rotating assortment of seasonal draught beers (prices vary) and wine by the glass ($8 instead of $10).

The big draw here is the snackables: At a venue known for its mini pizzas, guests can snag pita-sized flatbreads for $1. Let me repeat that: Just a dollar. More carnivorous types can grab a bacon pizza for $3, so we say raid your couch for loose change and just keep ordering until your eyeballs are floating in marinara.

PRETTY IN PEEKSKILL PROM is right around the corner!! What better way to ask your date than with a PB Happy Hour Pizza. 😉 🕠🻠. Special PB Prizes for BEST ASK / KING & QUEEN . “Best Ask” will go to the person with the most creative and public prom proposal. Be sure to use #promposal #peekskillbreweryprom. “King & Queen” will be crowned at the conclusion of the prom event! . Come join us for this special event on March 30th! We are turning back the clock and throwing an adult prom at the Peekskill Brewery. A portion of the proceeds is to help raise money for Operation Prom. A great organization that gets prom dresses and tuxes for low income students. . We’ll have OPEN BAR (for VIP ticket purchasers), DJ @joey_mercedes88 spinning the wheels of steel, a prom photographer doing 5×7 prints, Food Buffet, Boutonnières or Corsage, and Prize Giveaways. . Grab your tickets TODAY on the Peekskill Brewery website, or at the Tap Room Bar. . Come “dance your ass off” and support a good cause. . LINK IN BIO . #beer #explore #hudsonvalley #peekskill #findyourflavor #peekskillbrewery #ny #brewpub #pub #beergeek #beerstagram #craftbeer #fresh #nature #outdoors #draught #drinklocal #thinknydrinkny #nightout

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River Outpost Brewery/Fin & Brew

5 John Walsh Blvd

Lastly, we’re hitting you with a two-fer! One of Peekskill’s newest and most popular restaurants, Fin & Brew, holds happy hour from 4 p.m. to 6 p.m. Wednesday through Friday, which includes $5 draughts and $6 select wines.

Not enough for you? Head downstairs to the bar at River Outpost Brewery where during those same hours you can grab $4 pints as well as 25% off anything from the snacks menu, like oysters on the half shell, Bavarian pretzel bites, and lemongrass ginger braised chicken tacos!

Read More: Westchester Magazine’s Happy Hour Guide


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