A driving destination less than two hours from most major East Coast cities, the Poconos is the place for a road trip getaway.  

Our region has remained a place for travelers to escape and relax throughout the years. From outdoor adventure to historic landmarks, Pocono towns have something for everyone. Whether visiting during a day, midweek, or weekend vacation, our towns will welcome you with warmth and hospitality when you're ready.

For our third road trip, we're exploring the town of Stroudsburg. Located in the heart of the Pocono Mountains, Stroudsburg is known for its walkable downtown and historic charm. Main Street is home to wineries and breweries, authentic restaurants and boutiques. 

Be sure to call ahead to your destination for accurate information to confirm trip details. Read on and save future trip ideas for a three-day itinerary vacation to Stroudsburg, Pa. 

Day One: Learn and Be Active Outdoors

Morning: Start your trip in the Pocono wilderness. Walk the trails at Kettle Creek Environmental Education Center. Open from dawn until dusk, Kettle Creek's hiking trails are beginner-friendly and maintained with markers to keep you on the path. 

Afternoon: After your morning hike, visit Quiet Valley Living Historical Farm. Quiet Valley is a 19th century Pennsylvania German farmstead listed on the National Register of Historic Places. The summer tour season begins Saturday, July 4 through Labor Day, and runs Tuesdays through Saturdays from 10 a.m. to 4 p.m. and on Sundays from noon to 4 p.m. The grounds will be open until 5 p.m.

Travel into town and have lunch at Momento Restaurant. Keep it simple with a slice of pizza or order off their extensive Italian menu. After lunch, head to Kitchen Chemistry for dessert! They feature homemade cupcakes, macaroons and candy in addition to custom orders.

Evening: Ride your bike on the Levee Loop Trail for a twilight trek. The trail crosses through different parks in the area, and is accessible until 8 p.m.

Get cozy at an area country inn or bed & breakfast. Stroudsmoor Country Inn features overnight stays in their main inn, cottages, cabins and suites.

Day Two: Walk Around Downtown

Morning: Start off with a self-guided Stroudsburg Walking Tour. Discover National Register sites and landmarks throughout town. If you're interested in learning more history about Stroudsburg, make an appointment with the Stroud Mansion to dive deeper into the past.


Afternoon: Continue exploring downtown while shopping. From fresh produce to craft items, you'll find it here. American Ribbon Craft and Fabric is open Tuesday through Saturday 10 a.m. to 4 p.m. Dunkelberger's Sports Outfitter is open seven days a week, and features outdoor equipment, gear and clothing. Stop by the Monroe Farmers Market Saturdays through October, open 8 a.m. to noon, to grab whole foods, baked goods and more.

Treat yourself to an authentic experience at Siamsa Irish Pub. Located on Main Street, Siamsa offers favorite dishes from the Emerald Isle as well as great drinks.

Evening: The Sherman Theater is a historic entertainment venue downtown that hosts live concerts, old and new. Book your tickets for Saturday night acts like Kool and the Gang and Allman Brother’s Tribute.

Enjoy the convenience and accommodations of a downtown stay, and be close to all the action. Stay at The Penn Stroud on the corner of 7th and Main.

Day Three: Explore the Zip Code

Morning: Get your grub on with a tasty breakfast. Dine in or takeout at The Cure Cafe which serves up breakfast and lunch favorites from 8 a.m. to 2 p.m. every day except Tuesday. 

Afternoon: Satisfy your need for speed at S&S Speedways - Indoor Go-Karts. Make your reservation online to secure your spot on the track. Those 54” minimum height get the green light to go. 

Evening: Taste the region's flavor at our local wineries. Close to the track, try Mountain View Vineyard Winery's wine and food outside on the deck and property or drive back to Main Street to visit downtown wineries. Sit outside to enjoy beverages at RAW Urban Winery & Hard Cidery or order takeout wine from Tolino Vineyards. Journey to Cherry Valley to enjoy wine outside at Eagles Rest Cellars. Ask our wineries about their beer and spirits as well!



This itinerary is modeled after a Friday through Sunday schedule, but you could create your own Stroudsburg itinerary for any day of the week! We recommend that you call ahead to your destination before traveling to ensure nothing has changed. Masks are mandatory in all public spaces in Pennsylvania. Please continue to practice social distancing. 

Find more information on Stroudsburg hotels and things to do while visiting including maps of the town and surrounding areas. You can also explore other accommodations, activities and restaurants in the Pocono Mountains. 

Where will we go next? Check back next month when we take you on another road trip to our next town!

Things To Do

There's always something to do in the charming town of Stroudsburg. Whether picking out fresh…