The Best Trail to Tavern Pairings in New York City
Finding world-class taverns and bars in New York City is easy. It's finding the trails, which can sometimes be the challenging part. But if you know where to look—and in some cases, if you're willing to venture outside the city limits just a little ways—there are some surprisingly great places to hit the trail. And when you do, there's arguably nothing better than sipping on a nice, cold one after your time out in the wild. Here are five tried-and-tested, trail-to-tavern pairings that will be sure to make for a memorable (and refreshing) experience.
1. Bear Mountain | Defiant Brewing Company
Hiking in Bear Mountain is one of the most fun trail experiences you can have without going far from the city. Combined with nearby Harriman State Park, there are roughly 50,000 acres of mostly forested landscape and 235 miles of trails between them. With chunks of the Appalachian Trail in the park, plus plenty of other gorgeous single-track trails that are—especially on weekdays—rarely overcrowded, it's a breath of fresh air (literally and figuratively) if you're used to pounding pavement in the city.
Once you're done hiking, you can make your trip outside the city even more fun if you swing by the Defiant Brewing Company in Pearl River on your way back into the city after your hike. Pro tip: if you're not the designated driver home from this adventure, live large and try the O'Defiant Stout—the creamy, dark Guinness-esque beer will not disappoint, and will fill you up even if you did a 20 miler!
2. Prospect Park | Brooklyn Brewery
Brooklyn doesn't really call to mind nature and nice trails, but they do exist...you just have to know where to look. Head to Prospect Park for some on-dirt adventure in the nearly 3 miles of trails found in the park. It's a place with a similar vibe to Central Park (they were both designed by the same landscape architect), just way more scaled down and with far fewer people. It's also the best spot around for a need-to-get-on-trail urge when you don't have time to go out of the city.
3. Cunningham Park | Fillmore's Tavern
Cunningham Park, up in Queens, isn't just for mountain bikers: it's a great spot for trail runners and hikers as well. And the meticulously groomed and well-signed trails make its 358-acre expanse one of the best kept secrets in Queens. If you're trail running or casually strolling, be aware that it is a somewhat popular spot for mountain bikers, so listen for bikes behind you. Bonus mileage: if you need to add more miles, you're just a few blocks from Alley Pond Park, another great park with a combo of paved, doubletrack and singletrack trails weaving through wetlands, forests, and meadows.
And you might need that mileage if you're going to go two miles down the road to Fillmore's Tavern—a 102-year-old establishment with a ton of character—to indulge in a a beer or two during their fantastic happy hour, or if you're planning on having the Tequila Poppers (we won't blame you if you don't share them with your hiking buddy).
4. Inwood Hills Park | Hogshead Tavern
Inwood Hills Park has some of the best trails in the city. Winding singletrack allows great views of the Hudson River and skyscrapers, so it's a bit of a fairyland vibe where you feel completely alone in the middle of nowhere, but you're actually totally surrounded by the hustle of the city. The route from the tip of the park down to Hogshead—one of NYC's top taverns—is (dare we say) epic. You'll start winding through Inwood Hills, exploring and enjoying some of the serious stairs, before heading through neighboring trails in Fort Tryon as you head south four miles to Hogshead Tavern in Harlem. The selection of craft beer, whiskey, and uber-hip snacks (and brunch, naturally) make this the perfect post-hike destination, especially if you finish thirsty and hungry, and want some incredibly Instagram-able eats and drinks.
5. Sprain Ridge Park | Pete's Park Place Tavern
Twenty-five cent wings post-hike? Sounds like the best day ever, which is why you should venture north of Manhattan on Mondays to make a visit to the technical trails of Sprain Ridge Park (the terror of mountain bikers, and the training ground for those hoping to compete in more serious trail running events). After you've exhausted all of those trails and your legs, you can head to Pete's Park Place Tavern for beers and wings. It's the most traditional sports-bar environment out of the taverns we've checked out, but the ultra-casual atmosphere is welcoming even if you're a little bit sweaty, so it's worth the stop. And again—where in Manhattan will you find tasty wings for 25 cents?