At first glance, Stroudsburg, Pa., may seem like any other quaint Northeastern town with local restaurants, cute shops, and even a random KFC in the middle of Main Street. However, this community holds a rich history, boasting decades-old small businesses and surrounded by nature preserves, state parks, and outdoor amusements. It is the perfect destination for weekenders looking to explore the beautiful Poconos and Delaware River region.
Located near the Pennsylvania-New Jersey border, Stroudsburg serves as the seat of Monroe County and is one of the most populous towns in the Poconos, with approximately 6,000 residents. Its roots trace back to the 17th and 18th centuries, inhabited by Dutch and English settlers, and even earlier to the Munsee Lenape tribe, who have a history on the land dating back 10,000 years. The borough of Stroudsburg was officially founded in 1799 by Jacob Stroud, a colonel in the Revolutionary War.
How to Get to Stroudsburg
The journey to Stroudsburg is an adventure in itself, particularly if you opt for the scenic route. If you’re coming from the upper Hudson Valley, take I-87 down to Newburgh and then hop on I-84. While it may take a bit longer, consider taking the backroads through Ulster, Orange, and Sullivan counties for a cozier drive with picturesque views of small towns and foliage. As you make your way to Stroudsburg, you’ll pass through the stunning Delaware Water Gap National Recreation Area, which is worth a visit in itself.
For an unforgettable drive, take US-209 into the Poconos, which stretches from Kingston to Millersburg, Pa. The portion of the road that runs parallel to the Delaware River rivals the most scenic drives in the Hudson Valley. Picture driving under branches that bend over the road, surrounded by the Delaware Water Gap National Recreation Area, with trailheads scattered along the way. It’s a road trip dream come true!
Day 1: Brunch, Scenic Hiking, and Live Music
A great day in Stroudsburg starts with a hearty breakfast. Café Duet is a brunch lover’s paradise, offering a mouthwatering selection of breads, including ricotta toast, melted brie sandwiches, and Belgian waffles. If you prefer a lighter option, Quench Cafe and Juice Bar offers delicious smoothies to start your day on a refreshing note.
After breakfast, head to one of the nearby nature preserves or hiking areas for some scenic outdoor exploration. The Delaware Water Gap National Recreation Area, which spans 70,000 acres along the Delaware River, is just an hour’s drive away from Stroudsburg. Here, you can engage in various activities such as canoeing, hiking, fishing, cycling, and camping.
For a shorter hike, visit the tourist favorite, Bushkill Falls, also known as “The Niagara of Pennsylvania.” Traverse wooden bridges and trails over the water and enjoy the majestic waterfall surrounded by lush foliage. If you’re up for a longer hike, drive 20 minutes southeast to the Mount Minsi Trailhead in Worthington State Forest, a part of the Appalachian Trail. This moderately difficult 4.8-mile route offers breathtaking views of the Delaware River.
After working up an appetite, satisfy your cravings with some delicious ice cream from Zoe’s Ice Cream Emporium and Cafe, located inside Delaware Water Gap’s Castle Inn. Indulge in classic treats such as banana splits, floats, and malted shakes while surrounded by charming shops in this inn-turned-shopping plaza.
For dinner, visit the renowned Sarah Street Grill, considered the best restaurant in town by locals. Their extensive menu offers a wide range of options, including pizza, burgers, wraps, pasta, seafood, steaks, wings, and other classic American fare. After dinner, catch a live performance at The Sherman Theater, an old cinema turned music venue that hosts big-name acts every weekend.
Day 2: Farmers Market and Exploring Main Street
Start your second day in Stroudsburg with a visit to the Monroe Farmers Market, a beloved Sunday tradition for 40 years. From 8 a.m. to noon, you can browse stalls offering fresh produce, homemade cheese, bread, maple syrup, flowers, and more. Grab a cup of locally roasted coffee or a variety of teas from 7th Street Coffee to kickstart your morning.
After fueling up, take a leisurely stroll down Stroudsburg’s Main Street. This eclectic strip is home to a variety of businesses, including wineries, restaurants, an escape room, an Irish imports store, and even a brewery with axe-throwing. While exploring, be sure to make a pit stop at Main Street Jukebox, a unique record shop filled with an extensive collection of vinyl, CDs, and even VHS tapes. This small-town gem has welcomed famous rock bands who have performed at The Sherman Theater.
To cap off your visit, make time for a drink at one of Stroudsburg’s many establishments. Enjoy a glass of wine at The Renegade Winery or Tolino Vineyards, where live music sets the perfect ambiance every weekend. If you’re in the mood for a pub crawl, explore the town’s vibrant nightlife scene. End the night at Finola’s Irish Pub for traditional Irish fare and brews, or discover different flavors of ciders at Banter’s Hard Cider. RAW Winery, located in a 200-year-old building on Main Street, offers a compelling wine experience.
Stroudsburg, PA, is a hidden gem waiting to be explored. With its charming small-town feel, picturesque landscapes, and diverse range of activities and dining options, it’s the perfect destination for a weekend getaway. Start planning your visit to this Northeastern delight!
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