Peekskill lately is alive with trendy bars and restaurants, which of course means we sifted through its offerings to find, for your weekday drinking pleasure, four worth-your-while happy hours. Head over after 5 or, bucking trend, after dinner—Birdsall House and Table 9 offer two happy hour slots, the later starting at 9 and 10 pm, respectively. Wherever you choose, or whenever for that matter, these local favorites—in no specific order—are as much a testament to Peekskill’s emergence as a viable dining and drinking destination as they are to the timeless appeal of discounted drinks and appetizers.
92 Red Hook Rd
Happy Hour Monday through Friday, 4 – 6 pm & 9 – 11 pm
Willing to leave downtown for a drink? Good, we thought so, and you should be anyways, because Table 9, located just off Annsville Circle (you pass this on your way to Bear Mountain), has two – yes, two – happy hour times during which to indulge in half-priced appetizers and a limited but on-point selection of 16 oz. draft beers, house wines, well drinks, and martinis, all of which range from $3 to $5. And, by all means, pair your beverage with one or more decadent treats, like buffalo-stuffed chicken rolls or an onion ring stack, both of which go for $4 or $9 depending on your portion size.
970 Main St
Happy Hour Monday through Friday, 4 – 7 pm & 10 pm – 12 am.
Birdsall House, Peekskill’s trendy destination for live music lovers, hopheads, winos and foodies, also offers a dual weekday dose of inexpensive drinks and reasonably priced appetizers, first from 4 -7 pm, then from 10 pm – 12 am. The artisan-style food here is almost always delicious, so beware – after sampling the smoked pork nachos, served with cheddar cheese, black beans, blue corn tortilla chips, tomatillo salsa, and sour cream, or the grilled lamb sliders, complete with red onion jam, caraway mustard, organic challah buns, and Adirondack black wax cheddar, you might find yourself peeking at the dinner menu. All draughts and well drinks are only $5, and appetizers are $5 off at the bar.
5 John Walsh Blvd
Happy Hour Monday through Friday, 4 – 7 pm (Closed Tuesday)
Each day is a little different at the Harbor at Charles Point, located along the Hudson River. Harbor’s happy hour runs every weekday except Tuesday, offering half-priced house wine, well drinks, and beer. But we’re going to digress from happy hour for a moment and assume the view will entice you to stick around past 7 pm. Monday is Industry Night, meaning the restaurant/bar industry, so everyone to whom that applies enjoys half-priced appetizers and drinks. Also after 7 pm, Wine Wednesdays lands you a free wine with dinner entrees, while Twisted Thursday means $2 Twisted Teas and half-priced burgers. On Fridays, Bud and Bud Light bottles go for $3 when the live band is playing.
47-53 South Water St
Happy Hour Monday through Friday, 4 – 7 pm
Happy hour at the Peekskill Brewery is relegated to the Tap Room on the first floor, but we’re not complaining because, well, we’d recommend the Tap Room for happy hour anyway, and there’s no shortage of space there to enjoy the drink special: select 20-oz. pints of house brews for $5. They also offer a buck-a-shuck special on Blue Port Oysters, which is essentially a half-off deal. Of course, you’re welcome to step outside the discounted confines of happy hour and order from the main menu, which offers plenty of $5-to-7 snacks, such as pickled veggies and eggs, bacon caramel corn, olives and spiced almonds. Appetizers, such as pretzels and wings, range from $6-13.