Stroudsburg, Pennsylvania: Delaware Water Gap, Main Street & More

By VI | Disclosure: I use affiliate links

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If you’re looking for a charming mountain town with art, history, and year-round outdoor fun, I’d say Stroudsburg is a perfect pick. I’ve wandered its cozy downtown, explored nearby lakes and trails, and even caught a show or two—and I think you’ll love how it blends small-town warmth with plenty of adventure. Whether you're planning a romantic weekend or just want to unplug in nature, you’ll find yourself smiling the whole time.

Stroudsburg, PA Highlights:

Explore Downtown Stroudsburg: When I strolled downtown, I found art galleries, cafés, and the kind of little shops you want to get lost in. You’ll find something unique on every block.
Visit the Sherman Theater: I’ve seen live music and local events here, and if you go, you’ll love the vintage charm and energy inside. It’s the kind of place that makes a night out feel special.
Walk the Brodhead Creek Heritage Center and Trails: I spent a quiet morning walking by the creek—you should too. It’s peaceful, pretty, and perfect if you want to slow down and enjoy nature.
Tour the Monroe County Historical Association: I didn’t expect to enjoy this museum as much as I did. Inside the 1795 Stroud Mansion, you’ll learn the town’s story in a beautiful setting.
Attend a First Saturday Art Walk: If you time it right, you can join the locals and wander from gallery to gallery. I found live music, great food, and creativity everywhere—it’s such a fun evening.

Best Time to Visit Stroudsburg, PA

If you're planning a visit, I recommend going between April and October. I went in fall once and the foliage was unreal—every hike felt like a postcard. Spring and summer are perfect for outdoor festivals and exploring downtown. But I’ve been in winter too, and if you don’t mind bundling up, you’ll enjoy the snow sports nearby and the cozy charm of Main Street cafés.

How to Get to Stroudsburg, PA

If you are traveling by car: I’ve driven in from NYC and Philly—super easy. You’ll hop off I-80 and be in the heart of town in no time.
By Bus: I once took Martz Trailways from Port Authority in NYC and it dropped me right in town. If you want to relax and skip the car, it’s a great option.
By Plane: If you’re flying, I suggest landing at Lehigh Valley International Airport (ABE). I’ve used it before—it’s about 45 minutes away and super manageable.

Where to Stay in Stroudsburg, PA

Stroudsmoor Country Inn – I booked a weekend here and felt completely pampered. If you want a romantic stay with mountain views and delicious food, you’ll love it too.
Hampton Inn Stroudsburg/Poconos – When I needed something simple and comfy, this was my go-to. You’ll appreciate the pool, breakfast, and easy access to everything.
The Penn Stroud Hotel – I stayed here to be close to downtown, and you really can’t beat the location. You’ll be just steps from the shops and Sherman Theater—it’s ideal for exploring on foot.