Located in Monroe County in the picturesque Pocono Mountains, the borough of Stroudsburg offers a unique combination of beautiful, historical sites, newly emerging businesses and a vibrant social atmosphere.

Although initially settled in the early 1730s, the area now considered Stroudsburg was abandoned in the mid-1750s after a series of violent conflicts with Native American groups resulted in the deaths of more than 300 settlers. Forced to seek refuge in the relative safety of Easton, Bethlehem and Nazareth, the settlers did not revisit the area until the late 1760s.

Among those who returned in 1769 was New Jersey-born entrepreneur Jacob Stroud, who would later become the borough’s namesake. Purchasing a 300-acre parcel of land, Stroud transformed his property to include a gristmill, tavern and general store, and later built a large private residence at what is now Main and Fifth Streets.

Although his business enterprises were briefly interrupted by the Revolutionary War, in which he served as a Colonel in command of the Fourth Battalion District, Stroud and his wife Elizabeth raised twelve children and became arguably the most influential family in the area. Upon his passing in 1806, his son Daniel took over the majority of his business ventures and became a strong leader in the community. A lawyer by trade, Daniel arranged the charter for the name “Stroudsburg” and spearheaded the drive to have Stroudsburg declared the seat of Monroe County. He also played an instrumental role in spurring continued development in the area, and helped plan for growth by laying out new streets – many of which he named for his family members.

Today, Stroudsburg is home to just under 7,000 people. Its bustling downtown area still serves as the seat of Monroe County, and boasts more than two dozen restaurants, a half dozen art galleries and more than thirty specialty stores, many of which occupy historic buildings that serve as a reminder of area’s rich past.

Things To Do

Sherman Theatre

Relish the atmosphere of this historic theatre, built in 1928. Originally used as a vaudeville house and movie theatre, the Sherman was renovated and reopened in 2004 as a not-for-profit community theatre and concert hall. Today the theatre hosts performances by national acts such as Blues Traveler, Gin Blossoms and Weird Al Yankovic. Located at 524 Main Street, Stroudsburg. Check out their full schedule online at shermantheater.com.

Pocono Wine Trail

Enjoy the beauty of the Poconos while visiting seven family-owned vineyards and wineries, all conveniently located within a short drive of one another. The trail includes Mountain View Vineyard Winery & Distillery (Stroudsburg), Tolino Vineyards (Bangor), Franklin Hills Vineyard (Bangor), Blue Ridge Estate Vineyard & Winery (Saylorsburg), Sorrenti Cherry Valley Vineyards (Saylorsburg), Big Creek Vineyard (Kresgeville) and Brook Hollow Winery (Colombia, NJ). For more information, visit poconowinetrail.com.

Stroud Mansion

Build in 1795 by Stroudsburg namesake Jacob Stroud, this Georgian-style mansion is now home to the Monroe Country Historical Association. Stop by and visit their permanent exhibits, which highlight the history of Monroe County, or browse their special collections, which focus on the social, political and cultural life of the area. The mansion is also home to the Elizabeth D. Walters Library, which includes an extensive collection of unique genealogical materials and local history resources.

Olde Engine Works Market Place Antique Mall

Located at 62 North Third Street in the heart of Stroudsburg, the mall is home to more than 125 antique and collectible dealers. Their wide-ranging and unique offerings include retro fashions, furniture, jewelry, crafts, country primitive, textiles, pottery, folk art, gardening items, and more. For more information, visit their website at oldeengineworks.com.

Shop on Main Street

Main St. Jukebox

Located at 606 Main Street in downtown Stroudsburg, the store specializes in vinyl records, new and used CDs, original art, toys, turntables and rare and collectible items. Open every day of the week.

Vertical Earth Mountain Sports

The Pocono’s premiere mountain sports store and repair shop, Vertical Earth stocks everything you need for biking or snowboarding. Their knowledgeable staff can also make trail recommendations to help you get the most out of your experience. Visit them at 762 Main Street in Stroudsburg or check them out on the web at verticalearthinc.com.

Dawn of New York Boutique

Owned by Dawn Notaro, an inspired New York City stylist and graduate of the Fashion Institute of Technology, this boutique offers a stylish selection of dresses, tops and bottoms for women, as well as menswear and accessories. Stop in at 524 Main Street, Stroudsburg, or visit them on the web at dawnofnewyork.com.

Dunkelberger’s Sports Outfitter

Family-owned and operated since 1972, Dunkelberger’s offers a wide range of firearms and archery equipment, as well as gear and supplies for outdoor activities such as fishing, hunting, camping and hiking. Their apparel section includes a ladies boutique and a men’s shop, and they are an official Boy Scouts and Girl Scouts retailer. If you are new to outdoor activities, sign up for one of their “Dunk U” classes. Visit them at 585 Main Street, Stroudsburg, or on the web at dunkelbergers.com.

Stay the Weekend

Pocono Inne Town Magnuson

Located at 700 Main Street in downtown Stroudsburg, the hotel is within walking distance to area attractions such as the Sherman Theatre and Stroud Mansion, as well as many restaurants and shops. Originally built in 1833 by J. Stroud Hollinshead, the grandson of namesake Jacob Stroud, the hotel was initially called the Stroudsburg House and includes President James Buchanan among its noted guests.