Explore the Town of Stroudsburg: Road Trips to the Poconos

Day One: Stroll around Downtown

Morning:

Begin your visit by getting to know Stroudburg's roots! Sign up for a guided tour at the Monroe County Historical Association - Stroud Mansion Museum and Library, which is located in a beautiful colonial house built by Colonel Jacob Stroud, the town's founder himself, back in 1795. Learn about local history through the rotating exhibits. If you have ties to the area yourself, you can make a research appointment to examine the library's extensive genealogical collection.

When you're ready, head out onto the town's streets, some of which, such as Sarah Street and Anne Street, were named after members of the Stroud family. Admire the town's historic architecture on a walking tour. Use the digital guide to go at your own pace and learn about the beautiful brick buildings, many dating back to the 1800s.

Afternoon:

From the past to the present: pop inside the modern shops and boutiques that call the historic Stroudsburg storefronts home today! Dress to impress with a new ensemble from The Apple Tree, stock up on outdoor adventure gear at Dunkelberger's Sports Outfitter, satisfy your green thumb at The Potting Shed or pick out some sweet-smelling gifts at Pocono Soap. Stroudsburg shopping is one-of-a-kind, with many different independent stores and businesses located within easy walking distance.

The colorful murals lining Stroudsburg's streets are just the beginning of the community's arts and culture scene. Discover great events, festivals and shows at Sherman Theater. The seasonal Stroudsburg events calendar is packed with popular happenings like Winterfest in Downtown Stroudsburg, the Annual St. Patrick's Day Parade, Stroudfest and more.

Evening:

The flavors of Stroudsburg hail from all over the world! Sample international dishes at Los Tres Amigos, Shah's Halal Food, or Spice Route, just to name a few. No matter which cuisine you choose, you won't leave hungry.

There's no need to go far when it's time to turn in for the night. Book a room at the The Penn Stroud Hotel, situated in the heart of the downtown district. This historic property, originally built in 1833 by one of Jacob Stroud's grandsons, was recently updated with beautiful, modern guest rooms and upgraded amenities.

Day Two: Fun for All No Matter the Weather

Morning:

Prepare for another exciting day in Monroe County with a fresh breakfast. Grab a healthy, fruity smoothie bowl at Quench Cafe & Juice Bar, or enjoy a creative twist on breakfast classics at The Cure Cafe. If you're in the mood for coffee and a croissant, stop in Stroudsmoor Bakery & Café to peruse their delectable pastry case.

Get some fresh air and explore the beautiful farmlands and countryside surrounding Stroudsburg. Nearby Quiet Valley Living Historical Farm is a 19th century Pennsylvania German farmstead listed on the National Register of Historic Places. Reenactors bring the past to life with tours and seasonal events that families and history buffs alike will love.

Open daily year-round from dawn til dusk, Kettle Creek Environmental Education Center offers two and a half miles of well-maintained hiking trails, including the wheelchair-accessible Black Bear Trail. Keep your eyes open for wildlife as you stroll through forest and field.

Afternoon:

If the weather isn't cooperating for a day outdoors or you'd just prefer to stay inside, there are plenty of varied options for indoor fun in the Stroudsburg area. S&S Speedways offers the thrill of the go-cart track for new and returning drivers, with a minimum 54" height. Take on a communal cerebral challenge and see if your group can escape in time during an outing to Klues Escape Room.

Evening:

Journey into Stroudsburg's sister town, East Stroudsburg, for your evening meal. Crystal Street in East Stroudsburg hosts popular annual events like the Pickle Me Poconos Festival and Eastburg's Big Bang Fireworks and is also home to delicious eateries like Trackside Station Grill & Bar. Located further north near the Broadhead Creek, Cinder Inn Bar & Grill cooks up comfort food and daily specials.

Tucked away in the pastoral hills above Stroudsburg, the Stroudsmoor Country Inn offers a warm welcome to visitors. Stay overnight to experience the old-fashioned charm for yourself! The picture-perfect property is also popular for weddings, events and memorable meals at The Restaurant at Stroudsmoor Country Inn.

Day Three: Discover the Natural Wonders of Monroe County

Morning:

The namesake for the entire Pocono Mountains region is located not far from Stroudsburg! "Pocono" is a Native American word meaning "stream between two mountains," and it refers to the dramatic Delaware Water Gap. This geological feature is situated where the Delaware River cuts its way between Mount Minsi and Mount Tammany, and it shares its name with the historic borough of Delaware Water Gap. Set out for a hike over the Gap as you climb up Mount Minsi along the famed Appalachian Trail, or learn about the history of the area as you Tour the Castle Inn.

Afternoon:

When you've worked up an appetite, there are plenty of Delaware Water Gap restaurants where you can grab a hearty and handmade meal. Take your pick of pub favorites, grilled flatbreads, and signature sandwiches at Sycamore Grille. From lemon meringue pie to shoo-fly pie, from macaroni and cheese pot pie to apple pie, the Village Farmer and Bakery has an impressive selection of pies as well as baked goods, sandwiches and grilled foods.

Evening:

Don't leave the region without taking a trip along the Pocono Beverage Trail! From chic downtown Stroudsburg wineries RAW Urban Winery & Hard Cidery to nearby, scenic vineyards like Eagles Rest Cellars and Mountain View Vineyard Winery, kick back and toast to a great vacation. Let someone else take care of the transportation so you can enjoy the drinks: book a craft brewery or wine tour with Sip and Play Tours shuttle service.

Why not stay one last night under the stars in Stroudsburg? During the season, area campgrounds like Mountain Vista Campgroud give you the chance to linger by your own campfire. Cozy country inns like Cherry Valley Manor B&B provide the perfect retreat for a romantic getaway at any time of year.

Pick and choose your favorites from the itinerary suggestions above to craft your own Stroudsburg adventure! Find more information on Stroudsburg hotels and things to do. Why not extend your road trip and check out even more of the wonderful small towns throughout our four counties? See you in the Poconos!