7 Prettiest Downtown Strips In The Poconos

The Pocono Mountains of eastern Pennsylvania are known for their forested landscapes, scenic waterfalls, and outdoor adventure, but nestled within these natural wonders are small towns with abundant historic charm. These communities’ downtown strips offer more than quaint facades—they are living postcards where art galleries, historic landmarks, boutique shops, and local eateries combine to create welcoming, walkable experiences. This guide showcases seven of the most picturesque downtown strips in the region, each with unique attractions and inviting character. From well-known towns like Jim Thorpe to quieter treasures like Hawley and Milford, discover where heritage meets hospitality in the heart of Pennsylvania’s mountain country.

Jim Thorpe

Jim Thorpe’s Broadway Street is the centerpiece of one of America’s most beautiful towns, winding past steep slopes and grand 19th-century buildings that capture the grandeur of its coal-era boom. The Old Mauch Chunk Historic District enchants with its Italianate and Victorian architecture. Highlights include the Mauch Chunk Opera House, a restored 1881 venue that offers concerts and performances year-round. Nearby, the Asa Packer Mansion Museum immerses visitors in the legacy of the Lehigh Valley Railroad magnate. Black Diamond Gallery, featuring local artists, contributes to the town’s creative spirit. For a dose of nature, the nearby Switchback Railroad Trail offers hiking through a historic railbed with panoramic views.

Honesdale

Honesdale’s Main Street is a slice of classic Americana, with brick storefronts, lampposts, and independent businesses lining the walkable stretch. The Wayne County Historical Society Museum is a must-visit, with its full-size replica of the 1829 Stourbridge Lion, America’s first commercial steam locomotive. The Stourbridge Line offers scenic train rides through rolling countryside, particularly stunning in fall. The Wayne County Arts Alliance Gallery adds a modern twist to the town’s historic feel, featuring rotating exhibits by local creatives. Just minutes from Main Street, Prompton State Park provides outdoor lovers with trails, picnic spots, and opportunities to fish or paddle.

Delaware Water Gap

Downtown Delaware Water Gap may be small, but it is big on personality, reflecting the town’s long-standing connection to the arts and outdoors. The Antoine Dutot Museum & Gallery, housed in a restored 1850s schoolhouse, showcases local art and the town’s rich heritage. The nearby Deer Head Inn, America’s oldest continuously running jazz club, hosts top-tier performances and embodies the town’s creative soul. Downtown is also home to Village Farmer & Bakery, where homemade pies and locally made treats draw both hikers and musicians alike. All the while, the Delaware Water Gap National Recreation Area beckons with trails, waterfalls, and river views that make this area a beloved destination for hikers and kayakers.

Stroudsburg

Stroudsburg’s Main Street is the cultural heart of Monroe County, bustling with activity and creativity. The Sherman Theater, a restored 1928 venue, draws regional and national acts to its stage and often hosts community events and film screenings. The Gallery at 530 Main showcases local as well as national artists and offers workshops. Just steps away is the Renegade Winery, an urban winery with tastings and live music nights that give the town a festive flair. The Monroe Farmers Market, held in Courthouse Square every Saturday, adds freshness to the town’s pulse with produce, baked goods, and artisan products. Put it all together, and Stroudsburg’s downtown is clearly where heritage meets hip in the Poconos.

Lehighton

Lehighton’s appealing downtown, situated a stone’s throw from the Lehigh River, offers a range of shopping, dining, and entertainment options. Lehighton Outdoor Center is a hub for adventure-seekers, offering rentals and guided trips on the Lehigh River. A local favorite on First Street is Bonnie & Clyde Pub and Grill, set in a Prohibition-themed setting offering live music and classic American fare. Nearby, The Hofford Mill, a recently renovated historic mill, now houses a restaurant and event space with art installations and pop-up shops. For outdoor adventure, Beltzville State Park is a quick drive away, perfect for boating, hiking, or a quiet day at the lake.

Milford

Milford’s Broad Street is a postcard-perfect promenade of historic buildings and boutique storefronts framed by leafy sidewalks. Forest Hall, a Chateauesque-style masterpiece built in the late 1800s, now serves as a community hub for arts events and rotating exhibitions. The Columns Museum, home of the Lincoln Flag (stained with the president’s blood after his assassination), offers a powerful glimpse into Civil War history. At Milford’s Farmers Market, locals and visitors alike find fresh produce, baked goods, and handmade items. Just beyond the town center lies Grey Towers National Historic Site, former home of celebrated conservationist Gifford Pinchot, offering mansion tours and lush gardens that celebrate his legacy.

Hawley

Downtown Hawley radiates the quiet beauty of a riverside mill town with new life breathed into its historic bones. At the heart is the Hawley Silk Mill, a transformed 1880s factory now housing an arts center, eateries like the charming Cocoon Coffeehouse, and boutique shops. Just down the street, the Ritz Company Playhouse, a volunteer-run theater, stages lively performances throughout the year. Bingham Park, with its walking paths, events, and farmer’s market, provides a community gathering spot adjacent to the downtown. Just a few minutes from downtown, the picturesque Lake Wallenpaupack invites visitors to fish, boat, or simply unwind along its shoreline.

The Pocono Mountains may be best known for their natural grandeur, but their downtowns reveal a different kind of beauty—crafted from history, community, and small-town pride. From Jim Thorpe’s grand mansions to Milford’s artistic corners, these downtown strips invite exploration at a slower, more meaningful pace. They are places where cobblestone streets, heritage museums, local shops, and artistic spaces coexist with mountain views and river breezes. Whether you come for the architecture, the local flavor, or the natural setting, the downtowns of the Poconos are ready to enchant and inspire.