Exterior of a cafe with a striped awning and red tables and chairs in downtown Stroudsburg, Pennsylvania. Editorial credit: Here Now / Shutterstock.com

10 of the Most Charming Towns in Pennsylvania

The second state admitted to the Union back in 1787, the historically and culturally important commonwealth of Pennsylvania, is indeed a great place to encounter America’s past. Also known as the “Keystone State,” what truly makes Pennsylvania such a splendid place of discovery is its combination of historic allure, cultural delight, and natural beauty. Indeed, when visiting the State, there is never a shortage of exciting things to see and do. Although many will flock immediately to such famous cities as Philadelphia and Pittsburgh, the “Keystone State” is also home to many smaller towns, which are every bit as enticing as their big city cousins. Here, stunning natural landscapes, fascinating historic sights, and loads of special Americana reside in abundance, just waiting for a visit. So come see Pennsylvania across an exploration of these most charming towns, and step right into some of the absolute best of the Eastern United States.

Hawley

Church Street, Hawley, Pennsylvania
Church Street, Hawley, Pennsylvania. Image creditJillcarletti, CC BY-SA 4.0, via Wikimedia Commons

Picturesquely located along the Lackawaxen River, Hawley is a most charming community with a population of just under 1,300 residents. A scenic place to enjoy the great outdoors, this Poconos Mountain resort town offers guests plenty of fun opportunities to enjoy activities like hiking, cycling, swimming, fishing, sailing, and even kayaking. Meanwhile, just a short 30-minute drive, tourists will not want to miss the splendid “Niagara of Pennsylvania” or Bushkill Falls for a veritable photogenic pitstop!

Finally, the history lover can also appreciate Hawley’s offerings which include several landmarks that are included on the National Register of Historic Places. Amongst the properties of note are the Hotel Belvedere (1902) and the Hawley Silk Mill (1880), that create a unique sense of time and place. And with a pleasant climate that includes hot summers and cool winters, Hawley really is a wonderful place to visit throughout the year.

Middleburg

Beautiful brick building in Middleburg, Pennsylvania
Beautiful brick building in Middleburg, Pennsylvania, via File:Middleburg, Pennsylvania.jpg - Wikimedia Commons

The seat of Snyder County, the town of Middleburg, is beautifully located within the Susquehanna River Valley, and it can trace its foundational history to the late 18th century. Today, just over 1,300 inhabitants call this historic place home, where several preserved landmarks continue to transport guests back a few centuries. Explore such properties on the National Register of Historic Places like the County Courthouse and Old Stone Jail, while a number of early 19th century homes line the streets.

And, of course, as a river valley town, the scenic vistas in Middleburg are truly special. Here, lush greenery and mountain views in a comfortable climate make any visit here a delightful experience. Stop by the Shade Mountain Winery for some of the best in locally produced alcohols, while opportunities to go biking and hiking are the perfect ways to enjoy this serene Pennsylvania town.

Wellsboro

The downtown streets of Wellsboro still illuminated with authentic gas street lamps
The downtown streets of Wellsboro still illuminated with authentic gas street lamps, via George Sheldon / Shutterstock.com

Nearly 3,500 residents call Wellsboro home, the seat of Tioga County in northern Pennsylvania. A charming and scenic community with a modern foundational history dating to the early 1800s, Wellsboro is indeed a great place to enjoy the delights of nature and the cultural allure of 19th-century America. Visit the nearby Pine Creek Gorge, a gorgeous 47-mile area that is also known as the Grand Canyon of Pennsylvania. Here, awesome opportunities for hiking, cycling, and rock climbing are always popular, while the panoramas alone make it a photographer’s dreamland.

Meanwhile, back in town proper, the Historic District and Main Street are perfect for the history lover. Visit an array of properties listed on the National Register of Historic Places, including the First Presbyterian Church (1894), the Robinson House (1813), and the County Courthouse (1835), amongst many more. Add authentic and functioning gas lamps and Victorian-style architecture, and it is easy to see why Wellsboro is such a welcoming and pretty place to visit firsthand.

Williamsport

Weightman Block, Williamsport, Pennsylvania
Weightman Block, Williamsport, Pennsylvania

Established by the British in the 1760s, today, the town of Williamsport is a thriving cultural and financial center of north-central Pennsylvania. The seat of Lycoming County, home to nearly 28,000 inhabitants, Williamsport is indeed a historic lover’s delight, and visiting it can certainly create a sense of time travel to America’s foundational years. Explore many 18th and 19th landmarks throughout town while stepping into the famed Millionaire’s Row Historic District is like an overload of the past. Here, up to 260 distinct properties and other buildings are included in the National Register of Historic Places, while cobblestoned streets and charming shops and restaurants fill out the landscape.

In addition, Williamsport is also attractive for its pretty natural scenery and guests will not want to miss chances to spend time along the Susquehanna River. Here biking and jogging near the water remain popular, while several inviting public park areas invite all ages to enjoy the outdoors in a climate known for its hot summers and mild winters.

Easton

The Northampton Street Bridge over the Delaware River in Easton, Pennsylvania
The Northampton Street Bridge over the Delaware River in Easton, Pennsylvania

Near the border with the State of New Jersey, Easton is a charming colonial town that can trace its roots back to the 1730s! Today, this seat of Northampton County is home to a mid-sized population of just over 28,000, and it maintains an old-world charm in a modern world. Scenically located at the confluence of the Delaware and Lehigh Rivers, Easton remains a popular destination for a weekend getaway. Indeed, between its historic character and natural allure, Easton has proven itself to be one of Pennsylvania’s most charming places. Visit the special National Canal Museum to learn more about the region’s early economic growth and even take a canal boat ride that is drawn by mules! Then, stop by the historic Centre Square and marvel at the imposing Soldiers’ and Sailors’ Monument that honors the fallen of all conflicts.

Stroll though the pretty campus of Lafayette College (1826), while an afternoon at Bushkill Amusement Park is a fun way to delight the young and old of any travelling party. And, of course, as a river town, there is never a shortage of scenic things to do near the water. Go biking, hiking, and swimming while the popular Farmers Market sets up shop along the river’s edge.

Stroudsburg

The Restaurant District in Stroudsburg, Pennsylvania
The Restaurant District in Stroudsburg, Pennsylvania. Image credit Doug Kerr from Albany, NY, United States, CC BY-SA 2.0, via Wikimedia Commons

Stroudsburg is just some 75 miles from New York City, and indeed, this historic community is a great destination for any road traveler. Founded in the late 1700s, today, this seat of Monroe County is home to just under 6,000 residents, and it remains one of the most pleasing Poconos Mountain retreats. A great place to enjoy scenic scenes of nature stops like the McMichaels Creek and Glen Onoko Falls cannot be missed. Here, stunning cascades, quiet fishing areas, and moments of reflection make it an optimal destination to escape the busyness of big city life.

Meanwhile, at the Academy Hill Historic District, up to 180 properties are listed on the National Register of Historic Places. Including the County Courthouse (1890), the Woolen Mill (1893), and the Stroud Mansion (1795), this is definitely a place where stepping back in time comes to life. And with warm summers and mild winters, spending time outdoors in Stroudsburg is generally pleasing throughout the year, where charming bed and breakfast establishments and other shops are always ready to welcome guests.

Indiana

The cityscape of Indiana, Pennsylvania, in winter.
The cityscape of Indiana, Pennsylvania, in winter.

Also known as the “Christmas Tree Capital of the World,” the lovely town of Indiana serves as the seat of the named county in West Central Pennsylvania. Founded in the early 19th century, today, just over 14,000 inhabitants call this most charming place home, which is noted for its abundance of tree farms in town and the surrounding area. Indeed, during the Christmas season, these farms form an important part of the local economy, and the unique and refreshing smell of pines will surely attract all ages. Marvel at the many decorated trees during the Yuletide, while a special opportunity to choose and cut your own Christmas tree is a delightful experience.

In addition, Indiana boasts a warm summer climate, which makes it a nice stopover place outside of the festive season. Spend time on the beautiful campus of Indiana University of Pennsylvania (1875) while tasty eateries like Benjamin’s offer the best in American bistro favorites.

Bloomsburg

Market Square in the downtown area of Bloomsburg, Pennsylvania
Market Square in the downtown area of Bloomsburg, Pennsylvania. Editorial credit: George Sheldon / Shutterstock.com.

A pretty college town with a modern history dating to the mid-18th century, Bloomsburg is definitely a nice destination to enjoy true Americana in a small-town setting. The seat of Columbia County, with a modest population of just under 13,000 inhabitants, Bloomsburg is beautifully situated along the banks of the Susquehanna River, where terrific panoramas are never in short supply. Enjoy calm afternoon days swimming, jogging, and biking, while even just a casual stroll on the campus of Bloomsburg University of Pennsylvania (1839) may be enough for perfectly quaint memories. Add in several historic landmarks around town, such as inviting restaurants like Marley’s Brewery and The Blind Pig Kitchen, and the genuine charm of small towns in the USA comes alive in a most splendid fashion.

Hershey

Hershey Park in Hershey, Pennsylvania, USA
Hershey Park in Hershey, Pennsylvania, USA. Editorial credit: Lissandra Melo / Shutterstock.com

A truly sweet destination, the town of Hershey is known throughout America as the headquarters of the Hershey Chocolate Company. Established in 1903 expressly for the purpose of giving factory employees close access to their work, Hershey has grown from modest beginnings to a bustling mid sized town of some 14,000 residents. While all current denizens are now not necessarily linked to the chocolate company, this delectable enterprise remains Hershey’s main economic driver and star attraction.

Attracting thousands of tourists each year, wonderful landmarks like the theme park Hersheypark and Chocolate World are delightful for all ages, while behind the scenes tours and chances to buy some treats are always fun. Take photos at the Hershey Kisses street lamps, while a day at the ZooAmerica marvels with its fine collection of exotic wildlife. Amongst the other points of interest are the Hershey Botanical Gardens and the AACA Automobile Museum.

Lititz

Exterior view of the Julius Sturgis Pretzel Bakery in Lititz, Pennsylvania
Exterior view of the Julius Sturgis Pretzel Bakery in Lititz, Pennsylvania. Editorial credit: George Sheldon / Shutterstock.com.

With a colonial history dating to 1710, the town of Lititz is one of Pennsylvania’s oldest settlements, and today, nearly 10,000 residents call this lovely historic place home. A veritable time-machine-like destination to the 18th and 19th centuries, many preserved landmarks continue to populate Lititz’s streets. These include the Sutter House (1871), the Werner House (1762), and the Moravian Historic District, amongst others listed on the National Register of Historic Places.

In addition, inviting cultural events like the Fire and Ice Festival and the Summer Art Show reflect some of the best of Pennsylvania, while cute shops, restaurants, and other local businesses give Lititz a most appealing small town character.

Also known as the “Keystone State”, Pennsylvania is a most delightful place of historic intrigue, natural beauty, and special American charm that any age of traveller can appreciate. Home to a number of beautifully charming towns outside of the major centers of Philadelphia and Pittsburgh, these communities offer some of the very best of Pennsylvania in smaller, more intimate settings. From the historic centers of Lititz and Stroudsburg to the unique settings of Hershey and Indiana and the natural splendor of Hawley and Middleburg, these charming Pennsylvania locales are must-visits for anyone looking for a special set of memories. Wait no longer then, and come see the “Keystone State”, where wonder awaits everyone!

Share
  1. Home
  2. Places
  3. Cities
  4. 10 of the Most Charming Towns in Pennsylvania

More in Places