It’s the most wonderful time of the year! And the Pocono Mountains is ready to celebrate the cheer of the season with an event calendar full of holiday festivities. 

Pocono resorts, restaurants and downtowns are decking the halls for the month of December. Whether you want to meet Santa and his reindeer team or witness tree lighting and carolers, we’ve got the holiday treats for everyone!

‘Tis the season! Read on for a complete list of holiday happenings, and create your next family tradition in the Poconos.


Tree Lighting Ceremony
Downtown Stroudsburg
Date: Friday, November 29, 2019
Time: 5 p.m. to 7 p.m.
Cost: Free
Kick off the season with a seasonal tree lighting and get into the Christmas spirit in Downtown Stroudsburg! Enjoy a visit from Santa, caroling, candlelight ceremony, refreshments, and much more.


Winter Wonderland
Downtown Honesdale
Date: Friday and Saturday, November 29 - 30, 2019
Time: Varies
Cost: Free
New this year, Honesdale's annual tradition turns to its roots. It's a little known fact that the famous 'Winter Wonderland' song was written about Honesdale by native Dick Smith. The town celebrates this with the Annual Santa Parade, tree lighting, and seasonal fun. Small businesses will also host events for shoppers' browsing, and buying, pleasure.


Santa Express
The Stourbridge Line
Date: Varies through December 21, 2019
Time: 11 a.m., 1 p.m., 3 p.m. and 5 p.m.
Cost: $20/adult 13+; $10/children 12 and under; free for children 2 and under (lap seat)
All aboard the Santa Express! Kids will receive a present from Santa, a holiday size souvenir ticket and candy cane. Enjoy the panoramic winter wonderland scenery as you ride the rails in heated train cars. Don't miss your chance to ride with Santa; make your reservation today. 


Breakfast with Santa
Skytop Lodge
Date: Sundays, December 1 - 22, 2019
Time: 8:30 a.m. to 10:30 a.m.
Cost: $30/resort guests; $35/public; $20/children 5-12; 4 and under free (excludes tax and gratuity)
Join Santa for breakfast at Skytop Lodge! Sunday mornings will be filled with a bountiful breakfast buffet, holiday music and not only a visit from the big guy himself, but a ride in a horse-drawn sleigh!


Candlelit Christmas Dinner
The Settlers Inn at Bingham Park
Date: Friday through Sunday, December 6 - 8, 2019
Time: 6 p.m. to 9:30 p.m.
Cost: $95/person
Enjoy an elegant night out, and dine by candlelight in the beautifully decorated Settlers Inn Dining Room. For three enchanting evenings, the Settlers Inn will feature a farm-to-table menu and holiday entertainment. The Bradley Bunch will perform on Friday and Saturday and the Regional High School Choir will entertain on Sunday. Reservations are required. 


29th Annual Old Time Christmas
Quiet Valley Living Historical Farm
Date: Saturdays and Sundays, December 7 – 15, 2019
Time: 3 p.m. to 7 p.m.
Cost: $10/adult; $5/child 3-12
Step back in time, and learn about past holiday traditions on a 19th century farm. Bundle up for a lantern-lit farm tour, and witness costumed re-enactors preparing for the season. Experience songs and stories, holiday shopping opportunities, and a living Nativity scene in the barnyard. Tours run every 15 minutes, and take approximately 90 minutes to complete. Please call for group rates and reservations.


Jim Thorpe’s Olde Time Christmas
Downtown Jim Thorpe
Date: Fridays through Sundays, December 7 - 22, 2019
Time: Varies
Cost: Free; fees apply to some activities
See Downtown Jim Thorpe all decked out for the holidays. The community’s Victorian Olde Time Christmas weekends feature holiday displays, caroling and live entertainment, shopping at over 40 galleries and boutiques, children’s activities and free family events. Be sure to check out the annual tree lighting in Josiah White Park. Dress appropriately; some activities take place outdoors.


Annual Tree Lighting
Downtown Milford
Date: Saturday, December 7, 2019
Time: 4:30 p.m.
Cost: Free
Santa arrives in Downtown Milford during the annual Tree Lighting on December 7, 2019. There will be cookies, hot cocoa, and holiday caroling on the Milford Community House lawn. Remember to dress warm and bring your camera!


Hawley Winterfest
Downtown Hawley
Date: Friday through Sunday, December 13 – 15, 2019
Time: Varies
Cost: Free; fees apply to some activities
See historic Downtown Hawley draped in holiday décor in an event filled weekend. There will be festivities and activities all over town during the annual Winterfest! Look for dining specials, historic tours, fairs and sales, live performances, ice-carving demonstrations, and other festive things to do each day. Lodging packages are available.


Ugly Sweater Party
The Dock on Wallenpaupack
Date: Saturday, December 14, 2019
Time: 8 p.m. to Midnight
Cost: Free
Dust off your Christmas sweater from the back of the closet, and head to The Dock. Enjoy live music with friends this holiday season. Make sure to take ugly seriously; prizes will be given for the best. 


Ugly Sweater Party
Slopeside Pub & Grill
Date: Saturday, December 14, 2019
Time: 8 p.m. to 11 p.m. 
Cost: Free
Seeing double? Here's a second ugly sweater party - Slopeside’s fifth annual Ugly Sweater Party. Food and drink specials, a photo booth and DJ entertainment are all a part of the program. Anyone who dresses up will be entered for a chance to win cool giveaways! Prizes will be awarded for the ugliest sweater and the most festive outfit. Adults 21+ only.


Winterfest Brunch
The Settlers Inn at Bingham Park
Date: Saturday and Sunday, December 14 - 15, 2019
Time: 11 a.m. to 2:30 p.m.
Cost: $39/person
Stop by The Settlers Inn’s during Hawley Winterfest to refuel with a tasty meal. Winterfest Brunch features a delicious seasonal menu and holiday harp music by Kristy Chmura. Call for reservations.


Breakfast with Santa
Split Rock Resort & Golf Club
Date: Saturdays and Sundays, December 14 - 21, 2019
Time: 7:30 a.m. to 12:30 p.m.
Cost: $16/ages 13 older; $12/ages 5-12; $8/ages 4 and under
Enjoy a breakfast buffet with omelette and waffle station, and then take a trip to Santa's Workshop. The elves will assist with arts and crafts, and call Santa to take pictures. Reservations are recommended, not required. 


Breakfast with Santa
Silver Birches Resort
Date: Sunday, December 15, 2019
Time: 10 a.m. to Noon
Cost: $20/person; $12/children 12 & under; 2 and under free; $10/per Gingerbread House excludes tax and gratuity
Whether you are in town exploring Hawley Winterfest or not, come have breakfast with Saint Nick at Silver Birches. Stick around for extra fun with gingerbread house decorating. Call for reservations!


Gingerbread House Workshop
Blue Mountain Resort
Date: Sunday, December 15, 2019
Time: 11 a.m. to 2 p.m.
Cost: $5/person and $25/house
In its fifth year, Blue Mountain Resort’s Gingerbread House Workshop is sure to leave you feeling festive. Bring friends and family for a day of crafts, live music, and photos with Santa. All materials and hot cocoa are provided. Children 12 & under will even receive a gift from Santa! Donate an unwrapped toy, and be entered into a raffle. Space is limited.


Shawnee Traditions - Christmas Buffet
The Shawnee Inn and Golf Resort
Date: Wednesday, December 25, 2019
Time: Noon to 4 p.m.
Cost: $34.95/Adults; $29.95/Seniors 65+; $24/Youth 12-16; Children 2-11 $1.00/each year (example 7 years old = $7). Tax and gratuity not included.
This year, spend Christmas dining with friends and family at The Shawnee Inn and Golf Resort. This festive buffet features a carving station, prepared by their culinary staff. Be sure to call to make reservations. 


Winter Holiday Buffet
Kalahari Resorts and Conventions
Date: Wednesday, December 25, 2019
Time: 5 p.m. to 9 p.m.
Cost: $39.99/adults 13+; $15.99/children 4-12; under 3 free
Come hungry for Kalahari's winter holiday buffet. The spread features traditional fare of turkey, prime rib and roasted chicken plus many more chilled and hot enhancements. Be sure to save room for the beautiful dessert station! Call to make your reservations.


For more jolly happenings in the Pocono Mountains, browse our holiday and festival event calendars. Find special offers at our places to stay, so you can experience optimum holiday cheer! Be sure to check out other things to do during winter too!

It’s not too early to start making New Year’s plans! We’ll be blogging about those parties next week, but you can browse these coming events and special offers while you wait. Whether you’re looking to dress up for a party or suit up for the slopes, the Pocono Mountains is the place to be on December 31.

Happy Holidays from the Pocono Mountains!