8 Of The Most Captivating Small Towns In The Poconos

The Pocono Mountains in northeastern Pennsylvania cover four counties and over 2,400 square miles of forests, lakes, and valleys. The name comes from the Lenape word Pokawachne, meaning “stream between two hills.” Once tied to coal mining and early railroads, the region gained fame in the 20th century as the “Honeymoon Capital of the World” thanks to its many resorts.Today, the Poconos are defined by charming small towns. Jim Thorpe preserves Victorian architecture, Milford is framed by waterfalls, Honesdale celebrates its rail heritage, and Stroudsburg mixes historic streets with modern culture. With 11 of the most captivating small towns in the Poconos, visitors will find history, scenery, and hospitality and all the things make the Poconos so captivating.

Jim Thorpe, Pennsylvania

Tucked into the Lehigh Gorge, Jim Thorpe looks like a storybook town with Victorian rooftops set against steep mountain slopes. It began in 1818 as Mauch Chunk, a coal and railroad hub whose prosperity can still be seen in the ornate architecture that lines its streets. At the Asa Packer Mansion, visitors walk through grand parlors filled with carved woodwork and rich furnishings that reflect the wealth of a 19th-century railroad tycoon.

History continues a few blocks away at the Old Jail Museum, where preserved cells tell stories of the Molly Maguires, while the Mauch Chunk Opera House keeps the cultural spirit alive with concerts and shows. Outdoors, trails in Lehigh Gorge State Park offer waterfalls, river views, and bike paths that begin right at its edge.

Hawley, Pennsylvania

Set on the banks of the Lackawaxen River, Hawley grew in the 19th century as a canal and coal-shipping city, and many of its brick warehouses and mills still stand today. One of the best examples is the restored Hawley Silk Mill, now filled with shops and a café, giving visitors a glimpse of its industrial past in a modern setting. The walkable downtown is lined with boutiques, eateries, and vintage storefronts that make it feel both historic and lively.

Hawley is also a gateway to Lake Wallenpaupack, one of Pennsylvania’s largest lakes, where boating, fishing, and lakefront trails draw outdoor enthusiasts year-round. Enjoy cultural activities at the Ritz Company Playhouse, a community theater in a historic building, and the nearby Dorflinger Factory Museum, which preserves the area’s glassmaking heritage.

Milford, Pennsylvania

Milford sits along the Delaware River and feels like a living museum of American history. Founded in 1796, the town became a retreat for artists, politicians, and conservationists, many of whom left their mark on its handsome brick and stone streets. The elegant Grey Towers National Historic Site, once home to Gifford Pinchot, America’s first chief forester, still welcomes visitors with tours of its mansion and gardens. Strolling through the tree-lined downtown, you will find antique shops, galleries, and cafés tucked inside 19th-century buildings.Nature frames it beautifully, with Raymondskill Falls, Pennsylvania’s tallest waterfall, just a short drive away. Before you leave, check out the famous “Lincoln Flag” at The Columns Museum of the Pike County Historical Society.

Honesdale, Pennsylvania

Known as the “Birthplace of the American Railroad,” Honesdale made history in 1829 when the Stourbridge Lion became the first steam locomotive to run on U.S. tracks. Its role in transporting coal along the Delaware and Hudson Canal shaped its growth, and you can still see reminders of that industrial past in its handsome downtown and preserved rail lines. Today, the Wayne County Historical Society Museum tells that story with exhibits that include a replica of the famous locomotive.

Modern Honesdale streets are lined with boutiques, cafés, and galleries that host regular art walks, while events like the Roots & Rhythm Music Festival held in late summer bring the community together. Nearby, Prompton State Park offers hiking and kayaking just outside town.

Delaware Water Gap, Pennsylvania

Delaware Water Gap may be small, but its setting is dramatic, right where the Delaware River slices through the Kittatinny Ridge to form the famous “gap.” Founded in the late 18th century, the borough grew into a popular resort destination in the 19th century, drawing city dwellers to its mountain air and sweeping river views. Its quiet streets still reflect that heritage, with historic inns and charming storefronts that welcome travelers exploring the region.

Nature is the star here. The village sits at the gateway to the Delaware Water Gap National Recreation Area, where trails lead to overlooks, waterfalls, and stretches of the Appalachian Trail. The Antoine Dutot Museum & Gallery tells the story of its resort-era heyday, while the nearby Shawnee Inn and Golf Resort, dating back to 1911, continues the tradition of hospitality.

Stroudsburg, Pennsylvania

As the county seat of Monroe County, Stroudsburg has been a crossroads in the Poconos since the 18th century. Today, its historic core still features 19th-century brick buildings and a classic courthouse square, creating a downtown that feels both rooted in history and alive with activity. Visitors can browse antique shops, grab a meal at one of the many farm-to-table restaurants, or admire murals that celebrate the region’s culture.Art and community are central to Stroudsburg’s street vibe. The Sherman Theater has hosted performances since 1929 and remains a cultural anchor, while the Pocono Mountains Visitors Bureau highlights the area’s attractions from right in the city. Just outside Stroudsburg, trails at Glen Park and the Cherry Valley National Wildlife Refuge offer a chance to trade city streets for natural beauty in minutes.

Tannersville, Pennsylvania

Tannersville began as a 19th-century tanning and lumber settlement, but today it’s best known as one of the liveliest villages in the Pocono Mountains. Main Street still reflects small-town roots, yet the area has grown into a hub for shopping, dining, and mountain recreation. Travelers passing through often stop at the Pocono Premium Outlets, which pack more than 100 stores into a walkable setting.

Adventure is never far away. Just outside town, Camelback Mountain Resort offers skiing, snow tubing, and ziplining. For something quieter, the Tannersville Cranberry Bog Preserve, managed by The Nature Conservancy, features boardwalk tours through a rare glacial wetland.

Mount Pocono, Pennsylvania

Perched on the high Pocono plateau in Monroe County, Mount Pocono has been welcoming visitors since the late 1800s, when grand resorts and fresh mountain air made it a retreat for travelers from New York and Philadelphia. Though many of the original hotels are gone, the area remains a lively hub in the heart of the Poconos, with easy access to surrounding trails, waterfalls, and scenic drives. Its small downtown offers cafés, shops, and a welcoming base for exploring the region.Modern Mount Pocono is known for attractions that keep visitors entertained year-round. The Mount Airy Casino Resort brings nightlife, dining, and events, while nearby Kalahari Resorts offers one of the largest indoor waterparks in the country. For nature lovers, Tobyhanna State Park and Big Pocono State Park are almost 20 minutes away, offering lakeside hikes and panoramic overlooks.

From the Victorian streets of Jim Thorpe to the riverside beauty of Milford and the quiet trails around Blakeslee, the Poconos offer rural areas as diverse as the mountains themselves. Each community preserves its own story, whether through rail history in Honesdale, cultural events in Stroudsburg, or lakeside recreation near Hawley. Together, they reflect the region’s charming history, scenery, and hospitality. For travelers looking to slow down, explore, and experience northeastern Pennsylvania at its most captivating, these 11 towns are the perfect place to start.