Feeling in the mood to get out of the house and visit someplace new? Hop in the car for a road trip to Stroudsburg in the Poconos! Located less than two hours driving distance from major East Coast hubs like New York City and Philadelphia, the Pocono Mountains region of Pennsylvania is a haven of small town charm and outdoor adventure ideal for a quick road trip getaway at any time of year. Known as the "heart of the Poconos" due to its central location, Monroe County and its county seat of Stroudsburg are full of fun things to do and great places to stay.

 

Stroudsburg shines with a striking mix of small-town glamour, modern appeal and a beautiful, walkable downtown. A past top…

With vibrant downtown energy, a rich history and breathtaking natural beauty, Stroudsburg and its surrounding area offer something for everyone. Whether you're taking a quick weekend break or avoiding the crowds with a midweek escape, you'll find unique shopping, dining and attractions. Start planning your trip and find some inspiration with our three-day itinerary to Stroudsburg, PA.

 

Day One: Stroll around Downtown

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.

 

Stroudsburg Walking Tours

  • Main Street
  • (570) 421-7703

Enjoy a historic walking tour at your own pace. This walking tour is intended to guide you on your own discovery of Stroudsburg's historic treasures. At a leisurely pace, this is about a 60-minute walk. To make the walk shorter, focus on…

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 Apple Tree

  • 726 Main Street
  • (570) 421-2798

A Pocono Destination Boutique specializing in personal service and styling. The Apple Tree…

The Potting Shed

  • 931 Ann St
  • (570) 424-1174

Let The Potting Shed create something special for you! The Potting Shed is a beautiful…

Pocono Soap

  • 10 N 7th Street
  • (570) 421-1791

Pocono Soap is a unique gift shop featuring soap, candles and body care products made…

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

 

Pocono Arts Council

  • 530 Main Street
  • (570) 476-4460

The Pocono Arts Council supports the arts and culture by hosting exhibits, festivals and educational programs. ARTSPACE Gallery is a premier public fine art gallery run by Pocono Arts. This gallery raises funds for the Arts Council and the…

Sherman Theater

  • 524 Main Street
  • (570) 420-2808

The Sherman Theater has your ticket to unforgettable entertainment in the Pocono Mountains. From local acts and festivals to large-scale concerts featuring today's top performers, the Sherman Theater in Stroudsburg presents a full calendar…

Evening:

The flavors of Stroudsburg hail from all over the world! Sample international dishes at Churrasqueria La Morena BBQ, Del Tacos, Emilio's Place Restaurant or Spice Route, just to name a few. No matter which cuisine you choose, you won't leave hungry.

 

Del Tacos

  • 428 Main Street
  • (570) 420-1199

Serving up authentic Mexican food with delicious flavors and spices. Del Tacos provides a…

Spice Route

  • 3578 Route 611
  • (570) 664-8283

Spice Route is a specialty restaurant in the Poconos known for taste, ambiance, and…

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, 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

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 Inn Towne Bakery Cafe to peruse their delectable pastry case.

 

The Cure Café

  • 517 Main St
  • (570) 664-2888

Open for breakfast and lunch, this cozy eatery has a variety of options to choose from…

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.

 

Quiet Valley Living Historical Farm

  • 347 Quiet Valley Road
  • (570) 992-6161

History comes alive as period-dressed "family" members share their daily routine of chores and crafts on a 19th century Pennsylvania German farmstead. Nestled in the Pocono Mountains of northeastern Pennsylvania, Quiet Valley is open to the…

Kettle Creek Environmental Education Center - Hiking

  • 8050 Running Valley Road
  • (570) 629-3061

Explore the trails open daily from dawn to dusk. A hike at the Kettle Creek Environmental Education Center which provides hands-on and interpretive hikes and programs. Both public and private and tours are available. Over 2.5 miles of…

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. Little ones can bounce to their heart's content on the trampolines and inflatable obstacle courses at Pocolandia, while S&S Speedways offers the thrill of the go-cart track for new and returning drivers, with a minimum 54" height. Head to Downriver Brewing Axe Throwing to test your aim, or take on a communal cerebral challenge at Klues Escape Room.

 

Pocolandia

  • 344 Stroud Mall Road
  • (718) 612-3306

Pocolandia is an indoor play center for kids ages three to twelve. Everything is designed…

Klues Escape Room

  • 542 Main Street
  • (570) 688-6950

A truly unique experience for family, friends, or co-workers! Klues Escape Room is an…

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.
 

Trackside Station Grill & Bar

  • 50 Crystal Street
  • (570) 424-3200

With a family-friendly, sports themed atmosphere, Trackside Station Grill & Bar is a perfect stop to enjoy a lite bite, a hearty meal or a cocktail with friends. With an exceptional menu Trackside boasts classic pub fare and new takes on…

Cinder Inn Bar & Grill

  • 91 Mill Creek Road
  • (570) 421-1425

The Cinder Inn Bar and Grill is a great place to unwind with family and friends. When you're in the mood for good times and great food, be sure to check out the Cinder Inn Bar & Grill. Located in East Stroudsburg, PA, the Cinder Inn offers…

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 SCI - The Restaurant at Stroudsmoor Country Inn.

 


Day Three: Discover the Natural Wonders of Monroe County

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 during a ride with The Pocono Historic Trolley Tour.

 

Mount Minsi - Appalachian Trail - Hiking

  • (717) 258-5771

Hike a portion of the famed and historic Appalachian Trail in the Pocono Mountains! Head to the town of Delaware Water Gap to hop on the Appalachian Trail towards Mount Minsi. Choose from two routes for this challenging adventure - go rocky…

The Pocono Historic Trolley Tour

  • 20 Delaware Avenue
  • (570) 977-7731

The Pocono Historic Trolley Tour takes you on a one-of-a-kind journey back in time. Board the trolley and explore Minisink Hills and Shawnee, then travel through the National Recreation Area and into the heart of Delaware Water Gap. You’ll…

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. Sample prime meats like brisket, ribs and pulled pork as well as tasty sides like baked beans, Brussel sprouts and hush puppies at Joe Bosco Authentic Smokehouse BBQ. 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.

 

Joe Bosco Authentic Smokehouse BBQ

  • 55 Broad St Rear
  • (570) 664-9888

Joe Bosco takes great pride in hand-selecting their prime meats. Recognized by Trip Advisor as a 2022 Travelers’ Choice award winner for BEST BBQ. Everything is house-made and locally sourced. They smoke their prime beef over oak and sugar…

Village Farmer and Bakery

  • 13 Broad Street
  • (570) 476-9440

The Village Farmer and Bakery is a family owned and operated market and bakery right in the heart of Delaware Water Gap, PA. Watch the pies being made at this bakery and farmers market where all the baking is done on premises. Located in…

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 Pocono Daytripper.

 

Eagles Rest Cellars

  • 188 Eagles Rest Lane
  • (570) 242-3224

Visit this veteran, family-owned vineyard and winery nestled on a 200-acre farm in Cherry…

Pocono Daytripper

  • 18 N 7th Street
  • (570) 977-7731

Enjoy fun and adventure with family and friends. Pocono Daytripper is your destination for…

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.

 

Mountain Vista Campground

  • 415 Taylor Drive
  • (570) 223-0111

Mountain Vista Campground's wooded setting provides a perfect spot for your next vacation. Families will find secluded camp sites for tents and all types of RVs including big rigs. Cabins are also available. On-site amenities include free…

Cherry Valley Manor B&B

  • 115 Davis Court
  • (347) 601-0157

A luxurious B&B offering a delicious homemade breakfast, private hot tubs, large Jacuzzi spas, an outdoor pool, spacious suites with fireplaces in every room, five groomed acres with a gurgling pond, and much more. A perfect place for a…


 

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!

 

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