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The Best 2019 - 2020 Winter / Christmas Events in the Poconos

Many of us look forward to holiday entertaining in the Poconos. And if you’re expecting friends and family this year, here’s an article that can help you prepare your Poconos home for the holidays. Of course, not all winter activities take place at home. There are always plenty of activities to enjoy around the region—and around the state. Here’s a look at some of the best 2019-20 winter events in the Poconos.

The Pocono Winter Wine, Food, & Spirits Festival

The Pocono Winter Wine & Food Festival returns to the Sherman Theater this January! The 2020 Pocono Winter Wine & Food Festival will be held on Sunday, January 26 from 12:00 noon to 4:00 PM at the historic Sherman Theater in downtown Stroudsburg, PA. The Festival is designed to introduce attendees to a wide variety of local wines produced in and around the Pocono region and includes complimentary samples of local wine and fine cuisine from featured area restaurants. Explore the offerings of wine-related vendors and other artisan crafts. You can also take part in a mini paint-n-sip class! and more. The primary purpose of the event is to raise money for the non-profit Sherman Theater, to preserve and enrich the arts in the Poconos by providing a variety of shows from international acts to community theater to the newly developed Kids’ Series. Call 570-420-2808 for more information or visit

New Year’s Day Grand Buffet

Stroudsmoor's New Year's Day Grand Buffet has been served in the Main Inn Dining Room since 1984. Family and friends are invited to enjoy New Year’s Eve Stroudsmoor-style by sipping cocktails in the lounge before dining on a holiday buffet befitting a prosperous new year! Before saying goodbye to 2019, feast from the fisherman's and antipasto stations, the main buffet, carving board and desserts. Tenderloin of beef and honey-glazed ham will be presented on the carving board. Main buffet selections will include pasta, chicken, pork, and seafood. A spread of Stroudsmoor's signature desserts will complete the feast. Seating starts at 4 PM. Call (570) 421-6431 for reservations. Price: $46.95/person, half price for children under 10 (excludes beverages, tax, and gratuity). Check the website for additional information.

Outdoor Winter Activities

While plenty of people come for the skiing in the winter, there’s much more than just skiing in Pennsylvania’s winter wonderland. Sure, there are more than 185 ski slopes and trails to explore (with everything from beginner slopes to build confidence, all the way to steep expert mogul-filled runs. But the region also offers a lot more to enjoy. Here are just a few of the winter attractions that make living in the Poconos a winter wonderland. Here’s a post that tells you everything you need to know about skiing in the Poconos!


Take a toboggan or luge run down one of the slopes at the Adventure Center at Skytop Lodge in Skytop, PA (570) 595-7401.


This is a delightful and magical way to explore the region’s landscape. Give snowshoeing a try at Delaware State Forest Snowshoeing in Swiftwater, PA (570) 895-4000.


Want to race with the wind? Climb aboard a snowmobile, rev up the engine and ride till your heart’s content at Hickory Run State Park Snowmobiling in White Haven, PA (888) 727-2757.

Dog Sledding

Want something a little out of the ordinary? Jump on a dog sled and mush your way along trails behind a team of Siberian Huskies at Arctic Paws Dog Sled Tours in Skytop, PA (570) 216-2551.

Sleigh Rides

Looking for something a little more sedate? Take a trip through yesteryear when you wrap up in a warm blanket with your loved ones, breathe in the fresh, pine-scented air, watch the spectacular scenery glide by from your horse-drawn sleigh. Check it out at Carson’s Paradise Riding Stable in Mount Pocono, PA (570) 839-8340.

Winter Swimming

If you think great swimming and water fun are only summertime activities in the Poconos, you'll be delighted to explore these year-round water park options.

  • Check out their Snowland special for a magical winter wonderland experience.

  • Camelbeach Mountain Water Park: Camelback Resort, in the heart of the Pocono Mountains, introduces Camelback Lodge and Aquatopia– voted #1 Indoor Waterpark in the USA & one of the best resorts in the Poconos. You can also take advantage of the lodge’s mountain winter activities that include skiing and snowboarding.

  • Kalahari Resorts Indoor Waterpark: Come see 220,000 square feet of iconic water park fun at America’s largest indoor water park. Hear the whoosh as you zoom down one of the many hair-raising waterslides. Feel the splash of the wave pool, the thrill of the kids’ play area, or the rush of indoor surfing. You can also relax in your own private indoor cabana and enjoy a flat-screen TV, chaise lounges, refrigerator, security safe and much more.


Sherman Theatre, built in the 1920s and recently renovated, presents many of today's biggest shows. Complete with a full bar and wonderful restaurant, the Sherman Theater offers everything needed for a complete evening of entertainment. Audience and performers alike have been awed by the sound, comfort, and historic feel of this incredible performance venue. Scheduled winter events include the 2020 New Year’s Eve Party (The Amazing Decades) with DJ AJ Stack, a concert with Phil Vassar on January 9, 2020, and the Sherman Winter CraftFest on January 18-19, 2020. Click here for additional shows and events.Casino Theatre Entertainment Center features two modern movie theaters with digital projection and 3D capability. The entertainment center offers a 1950s-style malt shop and restaurant, featuring more than 70 flavors of Hershey's ice cream and special treats like homemade waffle cones, sundaes, malts, and egg creams. Food is served in the theater using special trays that fit into cup holders. The Casino is known for its "Dinner and a Movie" specials every Monday and Tuesday, featuring a home-cooked entree and movie ticket for just $11 ($14 if seeing a 3D movie). Visit their website for more details!

Adult Outings

Mount Airy Casino is a great place for adults to be adults. Enjoy gaming at the casino, fine dining at one of five different eateries and take in lots of great entertainment. Whether you want to rock out with Classic Rock royalty, Laugh out loud with comedy legends or swoon with Broadway’s Best, Mount Airy has a wide variety of big-name talent booked for you. Check here for upcoming shows. The casino offers several New Year’s Eve packages for this year.


If all those activities make you hungry, you won’t have to worry. There’s an abundance of great places to eat throughout the Poconos. lists the following as “The Poconos Five Top Restaurant Tables”: The Stone Bar in Snydersville, PA; Alaska Pete’s in Marshalls Creek, PA; Basso (Italian) in Cresco, PA; Peppes Bistro in Eagle Valley Corners; and The Dimmick in Milford, PA. You can also explore the offerings from several "farm-to-table" restaurants listed here. has designated the following restaurants as Diner’s Choice Winners of Best Overall restaurants based on thousands of OpenTable diner reviews.

Of course, the Poconos aren't just a winter wonderland. The region is a great place to be all year round. And what better way to have access to all the Poconos has to offer than to build your own dream home here. If you're looking for some ideas on what that could look like, take a look at some of the beautiful custom homes we’ve built in the area.  See what it would be like to enjoy all the winter activities—and the rest of the seasons in your new Poconos home!

Image by monicore from Pixabay

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