This Poconos Destination Is A Year-Round Escape Packed With Festivals, Cafes, And Music

Many visitors to Pennsylvania's Pocono Mountains flock to postcard-perfect destinations such as America's so-called "Little Switzerland," Jim Thorpe, or the adventure hotspot of Lake Harmony. However, a little more under the radar lies the hidden borough of East Stroudsburg, whose charm comes from its small-town authenticity and packed festival calendar. East Stroudsburg is a genuine year-round music town, its lively venues buzzing through snow and sunshine alike. The borough's café culture endures the region's drastic swings in temperature with ease. Whether you're warming your hands around a coffee in January or sipping lemonade in July, East Stroudsburg always gives you a reason to linger. When morning rolls around after a night of basking in the tunes, visitors can head to Taste 154 Café for a cup of joe served alongside breakfast favorites such as avocado toast, bagel and lox, or pancakes with organic maple syrup for those with a sweet tooth. Those rolling out of bed a bit later can enjoy a range of delicious brunches at Farmhouse Poconos.

After a day of mountain adventures, East Stroudsburg's nightlife scene doesn't just deliver with great food and drink options, but also fantastic live music. Foodies can catch Kitch-en Café's rotating specials from Thursday to Sunday, and browse local produce on Saturdays at the Monroe Farmers Market in nearby Stroudsburg. In the same borough, culture vultures staying for more than just the music can wander along to five different galleries during the First Saturday Art Walk at the start of each month.

With a population of fewer than 10,000 inhabitants, for a borough of its size, East Stroudsburg boasts a surprisingly packed festival calendar that rivals any other Poconos town. Chief among its signature celebrations is the Pickle Me Poconos Festival, which since 2019 has taken over Crystal Street each October. The event transforms downtown into a pickle-lover's paradise, complete with a beer garden and family fun at the Gherkin Garden kids' zone near the Dansbury Depot. The 2025 edition of the festival saw the addition of a pickleball court, allowing visitors to play the aptly named sport to burn off the brine. On the outskirts of East Stroudsburg's downtown, the two-day Pocono Food Truck Festival draws hungry crowds to the Shawnee Mountain Ski Area to enjoy artisan vendors and culinary delights.

For those seeking laughs amid the autumn leaves, Stroudsburg hosts the three-day-long NEPA Comedy Fest, featuring more than 40 comedians across over a dozen shows. The funky neighboring borough of Stroudsburg also serves up StroudFest, a lively Labor Day weekend celebration when Main Street fills with vendors and activities organized by the Sherman Theater. Self-proclaimed nerds can even revel in the fun at Sherma-Con, a videogame, board game, and cosplay extravaganza held each January at the aforementioned theater, complete with an after-party rave. Stroudsburg hosts the frosty fun of WinterFest, when more than 40 ice sculptures line its streets, with its main display at Courthouse Square, while October sees the town celebrate Halloween with Spooky Stroudsburg.

The borough's reputation as a live music hotspot is well-earned, with venues that keep the rhythm alive even away from East Stroudsburg's festivals. Derailed Taphouse, located on Crystal Street, is not only loved for its $1 Monday night wings, but also hosts live music every Friday and Saturday night, pairing local acts with a whopping 32 craft beer taps that are constantly on rotation. Just a few doors down, Trackside Station Grill & Bar at the historic Dansbury Depot offers hearty pre-gig grub with its pub fare and burgers in a family-friendly setting. Live music can also be found a few minutes down the road at Pub 447, near Gregory's Pond Park. It offers a chalet-style bar as well as an outdoor tiki area to be enjoyed in September and October. For twilight hour dancing in neighboring Stroudsburg, The Happy Hour Bar & Grill has music acts that start their sets at midnight most weekends, filling the dancefloor.

Around a 70-minute drive from Newark Liberty International Airport, East Stroudsburg is also within a two-hour drive of Philadelphia International Airport for those exclusively exploring the state of Pennsylvania. Travelers without a car can hop on a Martz Bus from New York City's Port Authority to neighboring Stroudsburg or the stunning Delaware Water Gap, just 6 miles from East Stroudsburg. There is also an hour-long Greyhound bus service from Scranton directly to Stroudsburg, just a stone's throw away from East Stroudsburg's downtown.