A Funky, Underrated Pennsylvania Borough Hidden In The Pocono Mountains Boasts A Lively Downtown

The Pocono Mountains flourish as a beloved destination where you can find everything from the picturesque views of Pennsylvania's tallest waterfall to five great train rides for viewing fall foliage. Hidden within this mountain region's treasure trove of gems is another destination that calls out to curious travelers. Complete with an adorable downtown district and historical charm, the town of Stroudsburg is a must-visit. Perfect for culturally-inclined jetsetters, Stroudsburg invites visitors to explore everything from the 18th-century architecture of the Stroud Mansion to the antique treasures of Olde Engine Works.

While best visited in autumn for a glimpse of that magnificent Poconos fall foliage, Stroudsburg stays active year-round with summer events like StroudFest (a free community festival), spring activities like the annual St. Patrick's Day parade, and winter celebrations like Quiet Valley Old Time Christmas (a holiday experience hosted by the nearby Quiet Valley Living Historical Farm). That said, prospective visitors should know that Stroudsburg can get frosty in the winter, with temperatures falling below freezing from November through March. If low temperatures don't scare you off, just make sure to read up on travel expert Rick Steves' best winter packing tips to help your trip go as smoothly as possible.

Downtown Stroudsburg has a lot to offer, from historic sites and art galleries to antique stores and local events. Get acquainted with the area with a scenic stroll starting at the Pocono Mountains Visitors Bureau. Located right on Main Street, this small visitors center has resources to help guide your travels. From here, walk to the historic Stroud Mansion, a 1795 home that architecture enthusiasts may recognize as a Georgian-style construction. Afterwards, learn more about local history at the nearby Stroudsburg Paulding Doughboy statue, a memorial to World War I veterans. Across the street, see an example of Richardsonian Romanesque architecture at the Monroe County Courthouse, which dates back to 1890. Then, end your walking tour at the Sherman Theater, a historic venue for the arts.

Once your history and architecture adventure ends, seek out Stroudsburg's artsy side. Gamut Art Gallery showcases an impressive collection within a 190-year-old historic building, blending local history with the arts. At Create & Be Art Studio, see creativity and diversity come together for a world of innovative art experiences. For more insight into Stroudsburg's art scene, plan to visit on the first Saturday of the month for the First Saturday Art Walk, held from 6 to 8 p.m. Can't make it? You can still experience the local creative culture through the public murals downtown. See if you can spot all 15 artworks around Main Street. Don't ignore the shopping options in downtown Stroudsburg, either. Antique hunters will love Olde Engine Works, a marketplace bringing together over 100 vendors selling vintage goods and collectibles. Other notable spots include Carroll & Carroll Booksellers, a charming independent used bookstore.

After perusing historic sites, art galleries, and downtown boutiques, what else is there to do in Stroudsburg? Plenty. Dive deeper into the town's culture during the Monroe Farmers Market, held in the Courthouse Square every Saturday from 8 a.m. to noon between May and October. Featured vendors include local farmers, bakers, baristas, florists, chocolatiers, beekeepers, and more. For a more hands-on activity, visit Main Street Makery for classes on everything, from soap and slime making to cookie decorating and bread baking. If you want to learn more about the region's history, make your way to Quiet Valley Living Historical Farm, a living history museum focused on 1800s Pennsylvania German agriculture. For something a little more modern but with retro vibes, visit Mayhem Amusements Arcade. While parents relive their gaming days at the pinball machines, kids can head over to GameQ Lounge, an e-sports lounge with PC, console, and virtual reality gaming options.

No trip to Stroudsburg is complete without sampling some of the local food, from restaurants and cafes to bars and wineries. For breakfast, stop at Café Duet for a cappuccino or cold brew with a fresh croissant. Diners craving more of a brunch vibe will love The Cure Café, which serves breakfast favorites like frittatas and pancakes, plus lunch fare like burgers and salads. At lunch, treat yourself to some excellent gyros and grape leaves at Cedars Mediterranean Grill. If you're craving tacos instead, swing by E'Z Taqueria. Before dinner, try the region's best wines at Eagles Rest Cellars, Renegade Winery, or Rowan Asher Winery. Then, end the day with takeout from Thai Orchid or a fancy dinner at Garlíc Restaurant & Bar for steak and small plates.