Stroudsburg Holiday Events

Holiday events Happening Next in Stroudsburg, PA

Poconos Freestyle Takeover 2: A Freestyle Christmas

 524 Main St, Stroudsburg, PA, United States, Pennsylvania 18360 20 Dec 2025
CHRISTMAS

Toys for Tots Collection

 Walmart East Stroudsburg 22 Nov 2025
HOLIDAY

Pet Photos with Santa

 1501 N 5th St, Stroudsburg, PA, United States, Pennsylvania 18360 29 Nov 2025
PICTURES-WITH-SANTA

Holiday Market Extravaganza

 1160 Clause Dr, Stroudsburg, PA 22 Nov 2025
HOLIDAY

Old Time Christmas 2025

 347 Quiet Valley Rd, Stroudsburg, PA, United States, Pennsylvania 18360 6 Dec 2025
CHRISTMAS

Grierfest Christmas Comedy Show

 522 Main St, Stroudsburg, PA, United States, Pennsylvania 18360 13 Dec 2025
COMEDY

Pet Photos with Santa

 AWSOM Wellness Center 6 Dec 2025
PICTURES-WITH-SANTA

Jessica Lynn's A Very Merry Classic Christmas

 Sherman Theater 6 Dec 2025
CHRISTMAS

Small Business Weekend

 931 Ann St, Stroudsburg, PA, United States, Pennsylvania 18360 28 Nov 2025
TRIPS-ADVENTURES

Small Business Saturday at Pocono Soap

 10 N 7th St, Stroudsburg, PA, United States, Pennsylvania 18360 29 Nov 2025
SHOPPING

4th Annual Gears for Gobblers Charity Ride 🦃

601 Main Street, Stroudsburg, PA 23 Nov 2025
FOOD-DRINKS

Wreath Making Workshop

 347 Quiet Valley Rd, Stroudsburg, PA, United States, Pennsylvania 18360 30 Nov 2025
WORKSHOPS

Thanksgiving Dinner - Stroudsmoor Country Inn

 257 Stroudsmoor Rd 27 Nov 2025
THANKSGIVING

Eighth Annual Community Thanksgiving | FREE

 First Presbyterian Church, Stroudsburg PA 27 Nov 2025
THANKSGIVING

Nutcracker Cafe | School of Visual and Performing Arts

11 Foundry St, Stroudsburg, PA 18360-1454, United States 5 Dec 2025
PERFORMANCES

*EVENT UPDATE* Triple M Treats® at Stroudsburg Area Music Supporters Holiday Craft & Vendorfest

 Stroudsburg High School 6 Dec 2025
CHRISTMAS-MARKETS-AND-FAIRS

Holiday Makers Market at Renegade Winery

 The Renegade Winery 6 Dec 2025
MUSIC