12 Prettiest Towns In The Poconos

Pennsylvania’s Poconos hold a chain of small towns where scenery and history flow together. Delaware Water Gap sits beside the Delaware River at the edge of the Delaware Water Gap National Recreation Area, so trailheads, overlooks, and riverside cafés share the same few blocks. Autumn brings hillsides and the river air turns crisp by dusk.

Up in Honesdale, rail heritage still shapes the streets: the town is celebrated as the birthplace of the American railroad, thanks to the 1829 run of the Stourbridge Lion steam locomotive. If you're interested in easy access to forests and lakes, plus local character that makes every stop memorable, read on!

Delaware National Gap

The charming small town of Delaware Water Gap, along the winding Delaware River, is a historic, over two centuries-old borough, right on the southern side of the Delaware Water Gap National Recreation Area. Find amenities and everything else you seek to stay comfortable while enjoying the 70,000 acres of natural beauty around you. With part of the Appalachian Trail running right here in the Poconos region, you can enjoy all-level hikes with sights like Pennsylvania's two easily accessible, tallest waterfalls. Don't wait to exchange the city soot for refreshing nature hikes in the pleasant fall weather and return for more recreation, photoshoots, and picnics next summer.

Delaware National Gap is a real year-round gem in the spectacular embrace of nature, with scenic fun and relaxation for every group. Find plentiful family pastimes like time travel aboard the cool Pocono Historic Trolley Tour or a self-guided ride through Minisink Hills and Shawnee, the two breathtaking back roads dressed in autumn colors. Visit the Antoine Dutot Museum & Gallery for beautiful legacy sights of Delaware Water Gap hospitality and hands-on experience at local businesses for food, unique gifts, and antiques, like Asparagus Sunshine and Village Farmer and Bakery. Tour the castle at the storied Castle Inn, where you can stay put for the night, or choose the Deer Head Inn with its legendary jazz performances.

Dingmans Ferry

This small town with a big heart at the doorstep of the state forest and national recreation area is full of bright experiences and cherishable moments for every group in the alpine atmosphere. Dingmans Ferry inspires a real getaway from everything you remember about the city, with some of the most beautiful hiking in the whole state and the best of the Poconos. Immerse yourself in all the scenery, like an engaging waterfall chase to Dingmans Falls, Fulmer Falls, and Deer Leap Falls, all easily accessible, to wipe the slate clean in the mist and feel recharged by the power of nature.

Find trails for all through the beautiful, dense forests with sparkling Delaware Water Gap cascades and viewpoints onto the mountain peaks. From the refreshing nature picnics and waterfall trails at the Delaware Water Gap National Recreation Area to the picturesque Dingman’s Ferry Bridge for another notable selfie, your muscles will let you know. Enjoy a day on the town through various shops and restaurants in a family-friendly atmosphere that charms with a cute name into a relaxing siesta with sights easy on the eyes.

Hawley

Hawley, a pretty town in the Poconos Lake Region, is the definition of picturesque. With year-round adventures, enjoy an outdoor escape from the city to explore the most unique sights and experiences. Take the famous "only here" bike ride right on the railroad tracks with the popular Soarin' Eagle Rail Tours amid stunning seasonal scenery all around. You can rent a two- or four-wheeled bike with Hawley's free bike share program and take your loved ones on a ride-along through the agricultural lands and farms that provide for all the delectable farm-to-table restaurants in town for an anticipating feast after.

Start your morning at the Cocoon Coffeehouse & Bakery and choose The Settlers Inn for a great stay and a restaurant serving dishes with fresh local flavors on a seasonal menu with a flair for innovation. Choose Tree Restaurant for craft beverages for dinner, or visit Wallenpaupack Brewing Company or Three Hammers Winery anytime for specialty brews and vintages with your Pocono Beverage Trail digital passport in your pocket! Nature, getting prepped for the fall season, welcomes you into a lush embrace of decorated trees for riverside trail hikes by the Lackawaxen River. Seek more fall colors just to the south at Lake Wallenpaupack that will have you back next summer for water recreation.

Honesdale

Rivaling for a spot among the most beautiful towns in Pennsylvania, Honesdale invites all the sightseers into its falltime embrace. Come to celebrate Honesdale's harvest and local heritage in between rolling Wayne County hills covered in fiery shades of garnet and gold. This quaint Northeast town, famous in the Poconos among rail and locomotive fans, hosts friendly residents, modern cultural sights, and a lively drinking scene.

This "Birthplace of the American Railroad," after welcoming the country's first steam locomotive in the 1800s, showcases a replica of the first "Stourbridge Lion" at the Wayne County Historical Society. Climb aboard the Stourbridge Line for an unforgettable spin through the fall foliage to bond over the old-timey charm and natural sights through the window. With a relaxed atmosphere and various train-themed excursions, Honesdale is a joy to explore for the entire family, with excitement for all. Check off the Twisted Rail Tavern and hit the brewery scene, including the popular Irving Cliff Brewery, among many others.

Jim Thorpe

This foremost city in the state and the Poconos region brims with small-town charm and spectacular mountain views. Not just the "Switzerland of America," but with a rich, 200-year-old history in its pocket and decorated streets with modern-day charms, it is no wonder that Jim Thorpe is so popular. Visit the real Main Street town with a beautiful downtown dotted with adorable shops in between famous museums like the Old Jail Museum and the Asa Packer Mansion Museum. Take a cultural stroll along its notable architectural feats, including St. Mark's Episcopal Church. A real Victorian-era epicenter and bearer of a former Olympian’s name, Jom Thorpe evolved from its anthracite coal roots as Mauch Chunk, a Lenape word for Mountain of the Sleeping Bear.

Gaining tourist followers early on, Jim Thorpe even rivaled the Niagara Falls region in the nation. Today, the charming town with a vibrant thoroughfare and nature is a year-round destination for the outdoors with biking, hiking, and paddling. Plan an imminent visit for the Halloween season in October with a weekend of the Jim Thorpe Fall Foliage Festival for food, crafts, and family fun. Wake up for an early morning paddle through fall colors in complete serenity along the D&L Rail Trail through Lehigh Gorge State Park to White Haven. Check out the Country Junction, the largest general store in the world, and choose one of the millionaire mansions turned B&Bs for an extravagant stay in this small town replete with experiences.

Lake Ariel

This one-of-a-kind scenic village on the namesake lake is a four-season getaway with recreational pursuits and modern amenities for every group. Seek respite from crowds with plentiful lakes around, like the 198-acre Roamingwood Lake, the 25-acre Deerfield Lake, and the 9-acre Brooks Lake, for waterside recreation with your loved ones. Take a refreshing hike along Ariel Creek all the way to the region's renowned Lake Wallenpaupack via Ariel Creek.

Needless to say, the town is a popular getaway during the summer, with the nearby Laurel Park Campground offering a family-oriented stay on a budget with tent camping and seasonal trailer sites with electricity and water. Find family entertainment at the in-town complex, complete with showers, a playground, a beach volleyball court, and even the Hideout Dog Park. You can join in various organized activities for all ages, such as flea markets, car shows, and large events, or roast your own marshmallows by the riverside or at your tent.

Milford

Despite being a speck in the Poconos with only 1,100 souls, Milford is hard to miss. The crown jewel of the mountainous scenery shines with small-town and nature charm on the Delaware River in Pike County. Meander your way through the old Victorian buildings in the hilly neighborhoods to the downtown area, where beloved local places attract visitors from near and far year after year. Set surrounded by fresh-air pursuits, you can enjoy the Delaware Water Gap National Recreation Area as well as Milford Beach, with many shops and restaurants post-nature.

Immerse yourself in the homey vibes and feel the stress melt away in a whole different atmosphere from the city's. Milford lets you choose your own brand of adventures for all tastes and scenery for every pursuit, like trails and picnics. Take a horseback ride to explore the area or enjoy trout fishing in the serene lushness along the Delaware River. The jaw-dropping views of the 400-foot-tall peaks above Milford make everything cozily encompass the charming little town in the valley below and rev up the adventurous for a scenic 45-minute hike to summit the Knob, with spectacular sights at sunset to linger in awe.

Pocono Pines

The town renowned for its natural beauty, Pocono Pines, is real eye candy and a dreamy escape into the best of the Poconos, proudly carrying the trademark name of the range and piney forests around. Enjoy the fresh scents on your daily perusal through downtown to the beautiful shores of Lake Naomi, with nature trails and spots to relax in awe. Find a concentrated scene of various shops and restaurants that keep this true year-round recreational epicenter lively throughout the year.

Escape the fast city pace for a respite like it was meant to be, with a pristine natural habitat maintained diligently for generations to come. Come in the summer for lakeside recreation and lush trails, and in the winter for Jack Frost and Big Boulder ski areas. The proud Poconos woodland community with friendly residents and a cozy feel amid the peaks welcomes you to join a wonderful family atmosphere of avid outdoor lovers. Find gracefully enhanced natural surroundings with amenities and developed trails for comfortable stays and treks along the Lake Naomi or Deer Trail Lake areas.

Stroudsburg

Stroudsburg, a proud town with rich local history, has a unique personality and small-town charm like no other. Find a conglomeration of sights and engagements in this vibrant community that is an all-in-one college town and an art hub with old Americana flair and world-wide cuisine. Just a small, largest town in the Poconos, with under 6,000 residents located in Monroe County, Stroudsburg lets you choose to call it what you may after your initial stroll through the vibrant sights downtown with artsy buildings and your first nature venture into the surrounding outdoors of the Poconos.

Find picture-perfect sighs at each step in a very historical place, as revealed by the architecture along Main Street. Browse your way through countless shops in old, painted buildings and check off a few restaurants before sightseeing the Stroud Mansion. The walkable town with a youthful ring in the air houses a renowned food scene to satisfy hungry, studious minds. Crawl through the pub fare with Thai, French, or craft beers or creative cocktails, perfect after a bike ride along Brodhead Creek’s path. Visit now for leisurely woodland strolls with colors on all sides, or seek tougher treks at Delaware Water Gap National Recreation Area along the riverside with water views.

Tannersville

Tannersville, a distinguished destination in the Poconos, offers a wide array of unique adventures for visitors to experience some of the region's finest sights. Visitors are encouraged to visit during the autumn season to witness the spectacular display of fall foliage at Camelback Mountain Adventures, the largest outdoor adventure park in the state, attracting visitors from across the globe for skiing and its waterpark. The park features a variety of activities, including a treetop ropes course, UTV tours, and a mountain coaster, allowing guests to select an appropriate level of excitement before gathering for a substantial family meal at Smuggler's Cove Restaurant or enjoying a drink at Barley Creek Brewing Company.

For those who are more inclined towards engaging in retail therapy, the Pocono Premium Outlets is a must-visit destination, alongside other prominent local businesses, offering popular goods such as mountain gear, sweaters, and scarves. The region's breathtaking mountain views are captivating in every season, situated just northwest of Stroudsburg, with both towns providing stunning vistas from elevations exceeding 2,700 feet above sea level. Finally, visitors can consider a winter holiday at Camelback Mountain Resort to indulge in skiing within the natural winter landscape that characterizes the Poconos, creating an ideal setting for winter sports enthusiasts.

Tobyhanna

Tobyhanna, a distinguished town within the Poconos, stands out with its rich historical heritage and scenic natural beauty, situated within a picturesque gap in the mountain range. Visitors are invited to immerse themselves in the charming environment, which is enriched with historical landmarks, retail establishments, and dining options offering stunning mountain vistas. It is advised not to delay; rather, one should visit promptly to experience the unparalleled autumnal scenery that adorns the quaint town and its surrounding natural preserves—ideal for scenic hikes under the early autumn sun.

A walk through the 18th-century sites, remnants of Tobyhanna's coal and lumber heritage, can be enjoyed amid the vibrant atmosphere of the town's many farmers' markets, showcasing seasonal produce and lively local culture. Patrons are encouraged to gather provisions for picnics at Tobyhanna State Park or to visit its renowned local waterpark, Kalahari Resorts, which attracts many families with young children. Equal in allure to the most charming small towns of the Poconos, it is evident that this gem holds a cherished place in the hearts of sightseers and remains a highly sought-after summer destination for families.

White Haven

White Haven is an essential stop whether you're passing through the Poconos or planning a weekend getaway for any group. This charming town, with its stunning views, offers a relaxing atmosphere and serves as the gateway to Lehigh Gorge State Park, renowned for white-water rafting and snowmobiling. Enjoy a 15-mile section of the Lehigh Gorge Trail from White Haven to Penn Haven Junction, where you can experience breathtaking winter scenery. Visitors can also take a scenic train ride in style, immersing themselves in a bygone era on a streamlined rail journey to Jim Thorpe—another must-visit town. The ride features live narration and engaging interactions. Be sure to visit the historic dining cars, reminiscent of those seen in Alfred Hitchcock’s "North by Northwest," for a charming meal that echoes the days of coal mining and railroads.

These pretty towns bestow a fun-filled vacation for all with a myriad of nature-filled activities as well as entertainment and culture downtown. From riverside and lakeside towns with rafting and sandy beaches for the summer to wintertime skiing resorts and thrilling adventures in between, you can always chill aboard a scenic train tour along the region’s railways. Come now for the beautiful fall season or enrich your holidays with the best downslope skiing. Find plenty of shopping, antiques, and gear stores, and unwind over a hearty meal or a brew pub.