A nature-filled weekend in the Poconos


This weekend, we’re recommending you check out a jazz club…in the woods. Hear us out. For many New Yorkers, thinking of the Poconos has them humming the saccharine jingle from the commercial for the “beautiful Mount Airy Lodge,” which ran endlessly on television back in the 80s. But for Lauren Chamberlain, the Poconos has a very different soundtrack — a jazz soundtrack. Lauren’s grandparents (and later, her mother and stepfather) used to own the Deer Head Inn, home to the oldest continuously running jazz club in the country. And like Eloise at the Plaza, Lauren grew up there, surrounded by musicians and artists. “I slept under a Steinway piano when I was a little girl because it was the only way I would go to sleep,” she says.

These days, Lauren owns a quirky antique store called Asparagus Sunshine, set right across from the Deer Head Inn in the center of Delaware Water Gap, a town that is not only famous for its jazz roots. It’s also considered the gateway to the Poconos — which is where we’re headed in this issue of The WeekEnder. But first, let’s talk location. The Poconos region is huge, stretching across four counties and millions of acres. In future episodes of The WeekEnder, we will revisit some of these parts, but for this weekend’s trip, we’re zooming in on Monroe County, which is home to some of the area’s most visited towns: Tannersville, Stroudsburg, and Delaware Water Gap.
This is from The WeekEnder series: local insider guides for new destinations a short drive from New York City, delivered to your inbox twice a month. Sign up here!
Here’s another thing to know: The Poconos has been updated since the days of disco, but it has still sustained some of its kitschy allure. (Think heart-shaped tubs and champagne baths.) You’ll find sleek waterparks and plenty of outdoor excursions, from hiking to zip-lining. And even Mount Airy is back with a new look and a casino, too. Let’s make our way to the mountains.
-Laura Begley Bloom, New York's Senior WeekEnder Writer
Where to stay

Resort report
The Poconos used to be the land of honeymoon hotels, but in the 90s, the love affair was over, as many of the old-school properties started to close and the new hits — complete with waterparks and casinos — started coming. Here’s our quick guide to the four major resorts in the area.
Best for: Calling all adventure seekers looking for action in every season — from ziplines and adventure courses in warmer months to skiing and snowtubing in winter.
Location low-down: Right at the base of Camelback Mountain.
Activity highlights: Bring on the superlatives: Pennsylvania’s only mountain coaster, Pennsylvania’s biggest outdoor waterpark, a massive indoor waterpark. And just in case you’re bored, there’s donut decorating, reptile shows, tie-dying, water balloon toss contests — the list goes on.
The food: You name it — a chophouse, a pizzeria with graffiti art by a former NFL running back, a brew pub, food trucks, and even a speakeasy-style game room and cocktail lounge for adults.
Pro-tip: Consider a midweek stay: Through May 27, the resort offers deals and tons of extras.
Best for: This one's for families. Kids will find endless entertainment, thanks to the resort’s branded (don’t cringe) “pawsitivity.”
Location low-down: A few minutes’ drive from the Tannersville outlets. But who’s going shopping when you’ve got all this fun?
Activity highlights: No boredom here, thanks to Howl at the Moon Glow Golf, an onsite Build-A-Bear Workshop, nightly story time, and a waterpark with a lazy river, wave pool, and more.
The food: A Ben & Jerry’s ice cream parlor sets the tone for the kid-friendly eats.
Pro-tip: You can’t go wrong with a themed suite. Choose from the KidKamp (with a tented sleeping area), the KidCabin (log cabin-themed), or the Wolf Den (complete with a cave).

Best for: The African safari-themed Kalahari appeals to all ages — kid-friendly arcade, dining and spa options for grown-ups, and three indoor waterparks with something for everyone.
Location low-down: Conveniently located just off I-380 at Pocono Exit 3.
Activity highlights: The largest indoor waterpark resort in Pennsylvania gives Kalahari its own bragging rights. The Gorilla Grove Treetop Adventures (minigolf, ropes courses, ziplines) is also pretty epic.
The food: Loads of choices — surf and turf at Double Cut, an Italian restaurant, a family-style buffet, snack bars, sweets shops, and more.
Pro-tip: Check out the special offers page on Kalahari’s website for good deals on bundled packages.
Best for: This quintessential honeymoon hotel was brought back to life as an adult-friendly casino resort.
Location low-down: A lakefront property surrounded by nature
Activity highlights: The ultimate gaming experience — more than 1,800 slot machines, 80 table games, sportsbook betting. Plus a spa, live entertainment, and a summer concert series.
The food: Big names (Guy Fieri’s Mt. Pocono Kitchen, Bistecca by II Mulino) and other options (sushi bar, pizzeria).
Pro-tip: For golfers, each of the 18 holes is modeled after an iconic championship course (Pebble Beach, Augusta National, and so on).
Beyond the resorts

For Music Lovers: Deer Head Inn in Delaware Water Gap
The oldest continuously running jazz club in the country also has 10 rooms for rent.
For History Buffs: Penn Stroud Hotel in Stroudsburg
This historic hotel from 1833 was built by a grandson of Jacob Stroud, founder of Stroudsburg. In 2020, new owners completed a multi-million-dollar renovation.
For Instagrammers: Cove Haven in Lakeview
You’re not coming here for luxury. This is the place to 'Gram the Poconos of the past: retro heart-shaped tubs and champagne baths.
For a Cheap Sleep: Poconos Log Cabin Vacation Rentals in various locations
Want to rent a log cabin in the woods? This is your resource.
Where to eat & drink

The Poconos isn’t exactly a culinary Mecca, but there are some worthy destinations scattered throughout the mountains.
Breakfast
Kitch-en in East Stroudsburg
The fluffiest and most unique pancakes (banana toffee with maple caramel syrup, banana bread with peanut butter), plus omelets, muffins, and other homemade treats.
Cure Cafe in Stroudsburg
It’s breakfast all day at this Main Street spot. Don’t miss the mushroom and goat cheese egg sandwich with avocado and bacon jam on a toasted brioche roll.
Cafe Duet in Stroudsburg
Skip Starbucks and head to this coffee shop that roasts its own beans.
Picnic to go
Village Farmer and Bakery in Delaware Water Gap
This 33-year-old farmstand was doing artisanal way before it was a thing. Any type of pie you can think of, they have it.

Casual bites
Zack’s Taco Shack in Tannersville
The best tacos in the Poconos.
Minisink Hotel in Minisink Hills
Biker bar with surprisingly good pub grub.
Barley Creek Brewing Company in Tannersville
A brewpub and distillery with an open-air biergarten.
Date night
Stone Bar Inn in Stroudsburg
Escargot, crab cakes, and all the ingredients for a delicious night out.
Momentos in Stroudsburg
Take your pick: Pizza on one side and fine dining on the other.
What to Do

You can’t think of a better place than the Poconos to take in the great outdoors, and the adventure options here are endless — horseback riding, ziplining, waterfalls, and more. Here’s where the locals go:
Kayaking
There are so many ways to explore the river in the Delaware Water Gap National Recreation Area, but according to Chuck Cooper, cofounder of Edge of the Woods Outfitters, kayaking is best. “It’s definitely the main attraction in this area,” he says.
Tubing
Camelback Lodge has its own lazy river, but during her downtime, where does the resort’s events and promotions manager, Lauren Brands, go? “My favorite thing to do: tubing down the river in the Delaware Water Gap during the summer,” she says.

Bird-watching
You’ll find the best birding along the 30 miles of river in the Delaware Water Gap area. “The wildlife is really abundant around here, especially birds of prey like bald eagles and hawks,” says Chuck Cooper.
Hiking
Fun fact: the Appalachian Trail runs through the Poconos and you can pick it up right in downtown Delaware Water Gap. “I love meeting all the hikers that come through — they have amazing stories to tell,” says Lauren Chamberlain, founder of Asparagus Sunshine.
Biking
Bring your own bike or rent one from Edge of the Woods Outfitters and head to the Joseph McDade Trail, a 30-mile bike path that runs along the Delaware River. “This land is our land — and it’s all public access,” says Chuck Cooper.
Weekend plans. Shared.
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