10 Best Towns in Pennsylvania for a Winter Getaway

Pennsylvania is home to the Mason-Dixon line, the birthplace of Hershey’s chocolate, the site of one of the bloodiest battles on American soil in Gettysburg, and one of the original founding states. This means that visitors looking to go on a Pennsylvania winter getaway will find history, good food, and a variety of other attractions in the towns that beautify the landscape.

That is in addition to the festive lights that adorn snow-filled villages, creating an old-fashioned American Christmas atmosphere. Those who anticipate stunning scenery and small-town charm won’t be disappointed when visiting the best winter getaway towns in the Keystone State.

Jim Thorpe

The small town of Jim Thorpe is nicknamed Little Switzerland for a reason. No matter how cold it gets, there is no escaping the cheer. Those visiting the Poconos Mountain town for the first time won’t be able to contain their delight when stepping aboard the Lehigh Gorge Scenic Railway train. December train journeys feature a jolly Santa and other winter-inspired characters to entertain the whole family. 

The historic downtown area reflects the joyful season with twinkly lights as far as the eye can see. Winter getaway enthusiasts should take a trip to Jack Frost Big Boulder Resort for skiing and snowboarding. In the dead of winter, the trails of Hickory Run State Park, north of Jim Thorpe, beckon hikers to come and explore, while the forests offer a memorable snowshoeing adventure.

Back in town, the Mauch Chunk Opera House brims with holiday entertainment while The Inn at Jim Thorpe awaits happily tired visitors with cozy fireplaces and views of a winter wonderland.

Wellsboro

During the winter season, right before the sleigh bells start ringing, the beautiful town of Wellsboro transforms into Santa’s playground. The snow-covered streets sparkle in the soft glow of the fairy lights, and the Dickens of a Christmas celebration awakens the seasonal spirit.

Visitors in search of an authentic American holiday experience can take a horse-drawn sleigh ride through these Christmassy streets or go skiing at the nearby Hills Creek State Park. Those who want to learn more about Wellsboro’s history can take a step back in time to the elegant Victorian era when they visit the Wellsboro House Museum.

At the end of a fun-filled day in the heart of the Endless Mountains, Wellsboro Inn on the Green offers private accommodations and an unforgettable breakfast in the morning.

New Hope

For a true small-town Christmas getaway, travelers should seek out New Hope along the Delaware River. Here, fantastic green spaces have been constructed around historic landmarks, like Bowman’s Hill Tower and Van Sandt Covered Bridge, which makes them the perfect places to wind down before the big holiday celebrations start. There is plenty of tubing, fishing, canoeing, and rafting to do before the start of the annual First Friday Gallery Walk. Those who want to get their ice skating on can do so on the frozen Delaware River Canal.

The James A. Michener Art Museum and New Hope Historical Society Museum put on an artful display for art and history lovers. Those who do not want to experience the ice and snow up close can wander the halls here and learn more about the history of this gorgeous little town.

New Hope is also not scrooge-y with its accommodation options, with New Hope Inn and Suites providing luxury rooms and a pool.

Smethport

Smethport only houses around 1,600 permanent residents, but travelers flock here during the winter when a blanket of snow provides the ideal backdrop for snowboarding and skiing. Situated inside the glorious Allegheny National Forest, this little Christmas town is one of the most scenic towns in the state and sits near the Kinzua Dam and Visitor Center.

Visitors can take a couple of days to explore the trails and waterfalls crisscrossing the forest or go boating on the Allegheny Reservoir. Take a self-guided tour through the Smethport Mansion District, where 30 luxury properties provide a glimpse into the lives of Smethport’s past inhabitants. And those who want to find out firsthand whether any ghosts roam in this part of Pennsylvania can take a night trip to the Old Jail Museum, rumored to be the state’s sixth most haunted location.

If the ghosts disappoint, the Mansion District Inn Bed & Breakfast will more than make up for the experience with a comfortable stay and delicious food.

Milford

Milford may not have any ghosts of Christmas past, but this stunning town offers snow-covered mountain views, frozen waterfalls, and twinkling lights along the riverfront. The ice rinks and designated skating areas in the vicinity are some of the best places to go ice skating with a hot chocolate in hand. The Delaware Water Gap National Recreation Area boasts picturesque hiking trails and cross-country skiing opportunities. Visitors can go on lazy winter boat rides on the Upper Delaware River.

The nearby Grey Towers National Historic Site offers information about the first Chief of the U.S. Forest Service, Gifford Pinchot, while the area surrounding Raymondskill Falls is great for taking festive photos.

Furthermore, the Hotel Fauchere, one of Milford’s mainstay boutique hotels, is a wonderful place to stay for a few nights, offering an on-site restaurant, and river views from most rooms.

Kennett Square

Kennett Square takes the Christmas spirit to new heights with its annual Festival of Lights at Longwood Gardens. Here, visitors will instantly warm up at the sight of a dazzling array of illuminated trees, flowers, and fountains. The light décor carries through to the town’s historic streets, where the Kennett Square Holiday Light Parade reverberates with the sound of carols and general merriment.

Winter travelers can go ice skating at the Kennett Square Ice Rink or hiking in the nearby White Clay Creek State Park. Within the town limits, the Kennett Flash offers concerts, while the Brandywine River Museum of Art displays vibrant American art.

The Bancroft Manor Bed & Breakfast gets in on the winter holiday fun each year and offers season treats, festive decorations, comfortable rooms, and warm beverages to keep the chill at bay.

Gettysburg

Gettysburg is one of the most historic towns in Pennsylvania. The hallowed grounds of Gettysburg National Military Park attract visitors throughout the year and during the winter season when they leave footprints in the snow and gather memories in their hearts. Those not fond of the old can take a licensed battlefield guide tour from the comfort of their cars. The Gettysburg National Cemetery inevitably evokes Civil War-era images while a winter hike through the adjacent Michaux State Forest allows a brief glimpse into how troops may have moved along tree lines during the conflict.

All the focus on history does not mean that Gettysburg ignores the Christmas holidays, however. Visitors can attend the Gettysburg Christmas Festival or indulge in a Dark Side of Christmas Tour, which offers a selection of ghost stories. In keeping with the historic theme over the holiday period, visitors can book a stay at the historic Gettysburg Hotel, which boasts superior service in the center of town.

Canonsburg

Canonsburg gives new meaning to the phrase ‘traditional Christmas.’ Residents here go all out during the happy winter holidays with mindblowing light displays throughout the town. There is a North Pole for the kids and plenty of opportunities to snap a fun picture with an elf or Santa himself. Canonsburg also sets up a holiday miniature train display, complete with Christmas scenes, snow-filled landscapes, and more.

Canonsburg’s aptly named Old Fashioned Christmas celebrations include a community tree lighting ceremony and Christmas Parade with floats, marching bands, and beloved holiday characters.

Visitors who want the entire Canonsburg holiday experience can book accommodation at Super 8, a budget hotel offering free breakfast. Those who prefer something more luxurious will find comfortable lodging at the Homewood Suites.

Hershey

Hershey is synonymous with delicious chocolate and winter family fun. Every December, the Hersheypark Christmas Candylane attraction features millions of lights, rides, and the now-iconic Hershey’s Kisses Tree. Families can explore the Hershey’s Chocolate World, tour the Hershey Factory, or take a leisurely walk in the Hershey Gardens.

However, there is more to Hershey than just chocolate. During the winter months, visitors can go tubing skiing, and hiking on the Horse Shoe Trail or through close by Memorial Lake State Park. ZooAmerica offers an up close and personal experience with gray wolves, mountain lions, black bears, and bobcats.

And when twilight sneaks up on the town, the Inn at Westwynd Farm awaits guests with sweet Hershey treats, an excellent breakfast, and relaxing fireplaces in each suite.

Strasburg

Strasburg offers a peaceful winter getaway of a different kind. Located in Amish Country, visitors envision the clip-clopping horse-drawn carriages before seeing them. Strasburg is one of the best places in the state for traditional Pennsylvania Dutch cuisine, and the delicious food theme carries through to the Strasburg Inn, where hot breakfasts accompany an affordable stay.

Strasburg is a quietly beautiful town where travelers can take a load off and enjoy the winter season. Take long walks through Strasburg Community Park or visit the Amish Farm and House. The Railroad Museum of Pennsylvania is on the carriage route, as are many Amish farms in the surrounding countryside. There is also the Dutch Wonderland amusement park, which offers award-winning holiday events like Merlin’s Magical Forest, Duke’s Blizzard Bash, and a light trail called Illumination Lane.

Pennsylvania is filled with a wealth of winter getaway towns for all types of travelers. There are tranquil mountain escape towns, glitzy Christmas parade towns, or small towns offering a big city experience. These ten destinations fit the bill perfectly and will provide an unforgettable winter experience for the entire family.