These Are Peekskill’s Must-Hit Happy Hours

Whether you’re finishing up a long day at work or kicking off the weekend, happy hour is the perfect time for both. There’s nothing quite like pouring a drink (or having someone do it for you) to unwind after a crazy day at the office. If you live or commute around the Peekskill area, we’ve done all the happy hour research you’ll ever need; all you have to worry about is what drink you’d like to sip on. Here are some places to go when you’ve clocked out and want a drink in your hand.

Taco Dive Bar

Ever wish that Taco Tuesday were everyday? The Taco Dive Bar is the place where those dreams come true. The building is part one of the two-part Peekskill waterfront property that also includes Buns-N-Bourbon, which is featured below. This is the place to go for all of your taco, nacho, and tequila needs since it’s the bar’s specialty. From Wednesday to Friday 5 to 7 p.m., hang out for happy hour where you can drink margaritas for $8 or order half-price drafts. If you’re worried you might not be in the mood for tacos during your happy hour visit, don’t be. There’s plenty of other foods to pick on, like chicken wings or hushpuppies, while you grab a drink or two. As an added bonus, it’s an easy 2-minute walk from the Peekskill train station.

55 Hudson Ave., Peekskill


- Advertisement -

This not-so-kid-friendly bar is part two of the Peekskill waterfront property that includes the Taco Dive Bar. This adult only section has the largest number of brown spirits on the wall, with 150 and counting, to satisfy any drinker. Happy hour runs Wednesday through Friday from 5 to 7 p.m. offering half priced drafts and a shot of the day. You can grab a seat at the bar or meet up with your squad at one of the hi-top tables to grab a drink and a fried-app snack. Order your drink of choice from the American brown spirits, canned beers from almost 50 states, or the draft beer tower selections. This establishment prefers that you choose to shoot whiskey (not guns); the occasional foul language is tolerated, the movies are questionable in terms of ratings and viewer discretion, sports are always available, and the music will be 100 percent classic rock a majority of the time.

55 Hudson Ave., Peekskill

Birdsall House

The tricky part about happy hours can be the small window of opportunity for when they’re offered. However, that’s not something you have to worry about at the Birdsall House. Not only does this spot offer a seven-hour happy hour Monday through Friday from 12 p.m. to 7 p.m., but there is also a late-night happy hour seven days a week from 10 p.m. to midnight. In other words, you can’t miss it! The earlier time slot takes place at the bar and in the beer garden at the picnic tables where draughts are only $5 and get $5 off appetizers, while the late-night version offers $3 select pints and $5 well drinks. Don’t stop at just a drink though: The happy hour appetizers offer plenty of picky foods that will surely satisfy your taste buds. Use your fingers to eat the melted cheese, salsa, and chips from the brisket nachos, or try a comfort food classic like the mac n’ cheese. Even if you’d rather stick to a healthy dish to make up for all the drink calories, there is a salad on the menu, too. This venue isn’t quite walking distance to the Peekskill train station — unless you don’t mind getting in a mile workout first. But, it is only four minutes by car, making carpooling or Uber-ing an easy options.

970 main St., Peekskill

The Hudson Room

Sashimi from The Hudson Room

- Partner Content -

While happy hour typically focuses on the drinks, there is plenty to eat during your time at The Hudson Room, too. Monday through Thursday from 5 to 7 p.m., is the time for happy hour here. Take a peak at the big menu of new American eats, like roasted butternut squash dumplings, classic buffalo chicken wings, and even sushi. If that doesn’t make your mouth water, it will when you see the rest of the items on the menu. The special during happy hour is $2 off all alcoholic beverages and food, except for the a la carte sushi. Don’t fret sushi lovers, there are still plenty of these options on regular menu, like the dragon fire roll or the tres color sashimi. Pick your dish, pick your drink, and let loose at The Hudson Room.

23 South Division St., Peekskill

Peekskill Brewery

The Taco Dive Bar isn’t the only place you can get tacos at happy hour on days other than Taco Tuesday. The Peekskill Brewery offers two-for-one 16-ounce beers and $2 tacos for a happy hour deal you don’t want to miss. From 4 to 6 p.m. Monday through Friday, you can feel safe offering to buy your pals the first round without emptying your wallet. It’s never been any easier! If you’re looking for the beer, but not really in the mood for the tacos, there are plenty of other snacks to eat. Take a bite of a Rockland Bakery pretzel dipped in beer cheese while you sip on that cold drink in your hand, or devour a spoonful of beer mac n’ cheese that would pair perfectly, too. That’s only a small taste of what the Peekskill Brewery’s menu has waiting for you.

47 South Water St., Peekskill

Read More: Westchester Magazine’s Happy Hour Guide


Our Best of Westchester Party is July 24!

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!

Holiday flash sale ... subscribe and save 50%

Limited time offer. New subscribers only.