What to Do in the Poconos!
Looking for something fun to do in the Pocono Mountains this weekend? Whether you’re into live music, outdoor adventures, or community events, there’s something for everyone. Here’s a quick roundup of what’s happening!
What’s the Weather?
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Saturday: Likely a morning thunderstorm and a chance of scattered thunderstorms in the afternoon. 80% chance of rain. High: 74°F, Low: 58°F
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Sunday: Mostly cloudy with a slight chance of showers in the afternoon. 22% chance of rain. High: 73°F, Low: 58°F
🛍️ Markets & Local Finds
Rise and shine with a visit to the farmers market. From fresh produce to artisanal goods, it’s the perfect spot to support local vendors and find unique treasures.
Monroe Farmers Market
📍 Downtown Stroudsburg
📅 Saturday, May 17 – 8 AM to noon
More info: Monroe Farmers Market in Courthouse Square
Josie Porter Farm Stand
📍 Cherry Valley, Stroudsburg
📅 Fridays – 12 to 6 PM
📅 Saturdays – 10 AM to 2 PM
More info: Josie Porter Farm Stand
Pocono Farmers Market
📍 Blakeslee (115 south of 80)
📅 Saturday, May 17 – 7:30 AM to 4 PM
Lehighton Farmers Market
📍 Downtown Lehighton
📅 Saturdays – 9 AM to noon
More info: Lehighton Farmer’s Market Facebook Page
Blue Ridge Flea Market
📍 Saylorsburg (648 Route 115)
📅 Saturday, May 17 & 18 – 6:30 AM to 3 PM
More info: Blue Ridge Flea Market
🎉 Festivals & Celebrations
Greek Fest of the Poconos
📍 Holy Cross Greek Orthodox Church (135 Stokes Ave, Stroudsburg)
📅 Thursday, Friday, Saturday and Sunday: June 5 – 8, 2025 from 4 PM (Sunday likely has early hours)
It’s that time of year again! Greek Fest! There will many Grecian delights such as: Mousaka, Pastichio, gyro, souvlaki, baklava cheesecake, and so much more! There is also beer, wine spritzers and ouzo for sale! Don’t miss the Greek dancing Thursday, Friday, and Saturday nights! OPA 
More info: Greek Fest of the Poconos Facebook Event
44th Annual Wind Gap Blue Grass Festival
📍 Mountain View Park, Wind Gap
🗓️ June 6, 2025 10 AM – 9:45 PM (last band)
🗓️ June 7, 2025 10 AM – 9:45 PM (last band)
🗓️ June 8, 2025 10 AM – 3 PM (last band)
Twenty-two bands, free camping, workshops, jamming and Blue Grass Academy for kids with food, crafts and vendors. Also featuring a Wernick Jam Class. Tickets available at the gate!
More info: Wind Gap Blue Grass Festival
34th Annual Great Taste of Pennsylvania Wine & Food Festival!
📍 Split Rock, Lake Harmony
🗓️ Saturday and Sunday, June 7 – 8, 2025, 12 PM – 5 PM
Sip, savor and celebrate Pennsylvania wines and food with full lineup of live music to enjoy a lively and flavor-filled experience in the Pocono Mountains. Bring a lawn chair or blanket and spend the afternoon celebrating the best tastes Pennsylvania has to offer.
More info: Split Rock Wine & Food Festival Facebook Event
✨ Special Weekend Events
2025 Spring Weatherly Hill Climb
📍 Weatherly, PA
📅 Saturday, June 7, 2025 – Timed Runs from10 AM to 4:30 PM; 6:30 PM Party at the Firehouse (tix extra)
📅 Sunday, June 8, 2025 – Timed Runs from 9 AM to 5 PM
A long-standing motorsport tradition in Weatherly, Pennsylvania since 1960! It is a one-mile race against the clock that challenges drivers to navigate the winding, uphill course along Hill Street. Food and drink vendors available. Cash only. Follow signs in town for parking.
More info: Weatherly Hill Climb
Wing Off!
📍 Sarah Street Grill – Stroudsburg
📅 Sunday, June 8, 2025 – 1 to 6 PM
The great annual Wing off returns hosted by Blue Ridge Hook & Ladder Volunteer Fire Company with live music!
More info: Wing Off Facebook Event
Touch A Truck
📍 Pocono Township Volunteer Fire Company – Tannersville
📅 Saturday, June 7, 2025 from 10 AM – 2 PM
Whether you’re a tiny tot or a big kid at heart, there’s something for everyone to enjoy at Touch-A-Truck.
More info: Touch A Truck Facebook Event
Levee Loop Trail Race 2025
📍 Dansbury Park – East Stroudsburg
📅 Saturday, June 7, 2025 – 8 AM
Benefit for Stroud Rec. 5k and 10k options available on beautiful trails – plus a new after-party this year: The Levee Splash at Dansbury Pool – tropical style!
More info: Levee Loop – info and tickets (Facebook Event)
Frozen Jr
📍 In2YouArts – Sherman Theater, Stroudsburg
📅 Saturday, 7, 2025 – Performances: 1 PM and 6 PM
📅 Sunday, 8, 2025 – Performances: 1 PM
📅 Friday,13, 2025 – Performances: 6 PM
📅 Saturday,14, 2025 – Performances: 11 AM
More info: In2YouArts Facebook Event
Arts & Craft Fair
📍 Bingham Park – Hawley
📅 Saturday, June 7, 2025 – 9 AM – 4 PM
FREE! Over 100 vendors with handcrafted items. 9 am Rain or shine. Musical entertainment in the Gazebo at 11 AM.
More info: Arts & Craft Fair
Punchlines: Comedy Live
📍 Pocono Cinema & Cultural Center – East Stroudsburg
📅 Saturday, June 7, 2025 – 7 – 10 PM
Featuring Anthony Fuentes, Julio Diaz, Onika Mclean, and Eric Nieves at Comedy Live! Special Guest Rafael G’ee.
More info: Punchlines Facebook Event and Tickets Link
Pick Your Own Strawberries
📍 Heckman’s Orchards – Effort
📅 Call 570-629-1191 for PYO availability; store open daily from 9 AM – 6 PM
More info: Heckman Orchards
40th Anniversary Gala Concert with Festival Orchestra
📍 St. Joseph Roman Catholic Church – Jim Thorpe
📅 Saturday, June 7, 2025 – 3 PM
Hosted by The Bach & Handel Chorale. Tickets may be purchased from the chorale office at 570-325-4794, Sound Check records on Broadway in Jim Thorpe and The Beacon Diner on Route 309 in Hometown
More info: The Bach and Handel Chorale
JCW 2nd Annual Show for Veterans and Valor
📍 Sugar Hollow Farms – Effort
📅 Saturday, June 7, 2025 – 1 – 4 PM
Hosted by JCW Outdoor Power Equipment. 2nd annual show in support of our Veterans and awareness for Valor & Band of Brothers.
More info: JCW Facebook Event
Monroe County Master Gardeners Plant Sale
📍 724 Phillips St – Stroudsburg
📅 Saturday, June 7, 2025 – 10 – 2 PM
Hosted by Penn State Extension Master Gardeners, Monroe County.
More info: Master Gardeners Facebook Event
🎶 Live Music & Entertainment
🗓️ All Weekend
Music on Main – Stroudsburg
🕕 6:00 – ??? PM
📍 Main Street, Downtown Stroudsburg
Kick off your weekend with the sweet sounds of live local musicians performing right on Main Street. This beloved Friday and Saturday night tradition is a great excuse to grab a bite, stroll the shops, and enjoy that classic small-town vibe under the evening sky.
More info: Discover Downtown Stroudsburg
Sherman Theater – Stroudsburg
📅 🕕 Various Dates and Times
📍 Main Street, Downtown Stroudsburg
Always something going on at the Sherman! Check out their website and get your tickets!
More info: Sherman Theater
Derailed Taphouse – East Stroudsburg
📅 Friday, June , 2025 at 8 – 11 PM
📍 Derailed Taphouse, Crystal Street, East Stroudsburg
Jason Knorr
More info: Derailed Taphouse
Warrior Bar and Grill – Stroudsburg
📅 Saturday, June 7, 2025 at 7 PM
📍 Warrior Bar and Grill, Lower Main Street, Stroudsburg
Flyin’ Blind Duo
More info: Warrior Bar and Grill
Happy Hour Bar and Grill – south Stroudsburg
📅 Saturday, June 7, 2025 at 7 PM
📍 Happy Hour Bar and Grill, south Stroudsburg
Cody James
More info: Happy Hour Bar and Grill
Stonehaus Meadery – Stroudsburg
📅 Saturday, June 8, 2025 at 8 – 11 PM
📍 Main Street, Downtown Stroudsburg
80’s Night with DJ Chaz
More info: Stonehaus Meadery
ShawneeCraft Brewing Company – Shawnee
📅 Saturday, June 7, 2025 at 7 – 10 PM
📍 ShawneeCraft Brewing Company, Shawnee-On-Delaware
Earth Song
📅 Sunday, June 8, 2025 at 7 – 10 PM
Derailed
More info: ShawneeCraft Brewing Company
🌿 Outdoor Adventures
National Trails Day Hike at Fieldstone
📍 Fieldstone Farm Preserve, 512 Devil’s Hill Rd, Cresco, PA
📅 Saturday, June 7, 2025 – 10 AM – 12 PM
Hosted by Pocono Heritage Land Trust. Go for a hike!
More info: Tickets
Pocono Whitewater Adventures
📍 1519 State Route 903, Jim Thorpe, PA
📅 Everyday
Dam release this weekend and until June 15, 2025!
More info: Pocono Whitewater Adventures and Bookings
Fishing in the Poconos
📍 Pocono Mountains, PA
📅 Everyday
Looking for some fishing places? Here’s some ideas from one of our beautiful resorts, Mountain Springs Resort.
More info: Mountain Springs Lake Resort Fishing Spots
🚂 Transportation Activities
Pocono Day Tripper
📍 East Stroudsburg, PA
📅 Friday, Saturday, and Sunday
Hop on/Hop Off Wine Tours, Foodie Tours, Slate Belt Wine Tours and Historic Tours
More info: Pocono Trolley Day Trips
Lehigh Gorge Scenic Railway
📍 Jim Thorpe, PA
📅 Friday, Saturday, and Sunday
Explore the Poconos by rail on the historic train. Bike train available on certain weekends throughout the season but start May 17 and 18.
More info: Lehigh Gorge Scenic Railway
The Stourbridge Line – Dinner Trains!
📍 Honesdale, PA
📅 Friday, Saturday, and Sunday
Many events to plan for but this weekend, the Princess and Superhero train event is on Saturday, May 17, 2025 at 3 PM.
More info: The Stourbridge Line – events and dinner train
Pennsylvania Rail Bike
📍 Hawley, PA
📅 Friday, Saturday, and Sunday
Scenic and recreational railbiking adventures. Experience the 10-Mile Excursion (Approximately 2 hours). It is perfect for those seeking a balance between exploration and leisure. Bike train available on certain weekends throughout the season. See their website.
More info: Ride a Bike on the Rails
🍷 Wineries and Vineyards
Blue Ridge Estate Vineyard & Winery
📍 Saylorsburg, PA
📅 Monday to Sunday
Many events throughout the year including Barrel Tasting, Underground Dinner Experience, Murder Mysteries and so much more!
Friday Night a la Carte Dinner – 5:30 to 8 PM
Just pop by! Dinner provided by Taste of Italy
Live music from 5:30 to 8:30 PM
Saturday Night a la Carte Dinner – 5:00 to 8 PM
Stop in! Dinner provided by Angels Café & Catering
Live music from 5:30 to 8:30 PM
4th Annual Nashville Invasion
Saturday – 3 – 8 PM
FREE! All the way from Nashville! Wild Bill and the Bruisers will provide an absolutely, amazing and unforgettable performance that you will be sure to enjoy!
More info: Blue Ridge Estate Vineyard & Winery
Eagles Rest Cellars
📍 Stroudsburg, PA
📅 Sunday, 2 – 5 PM
Latin space funk music with Sol Katana!
More info: Eagles Rest Cellars
M & M Vineyards
📍 Bangor, PA
📅 Friday, Saturday, and Sunday
Where every bottle tells a story! Guided Wine tasting experience with the owner/winemaker or take a Self-Guided wine tasting tour. Walk-ins welcome!
Indo-Chinese Food & Wine Pairing
Next event: Friday, June 13, 2025 from 5 – 8 PM
More info: M&M Vineyard
Mountain View Vineyard, Winery, Brewery & Distillery
📍 Stroudsburg, PA
📅 Sunday thru Friday: 11 AM – 6 PM; Saturday: 11 AM – 9 PM
Production and Vineyard Tour
Saturday, June 7, 2025 from 1 – 1:45 PM
Goat Yoga & Wine
Sunday, June 8, 2025 at 12 – 1:30 PM
More info: Mountain View Vineyard
Sorrenti’s Family Estate
📍 Stroudsburg, PA
📅 Wine Tasting: Friday/Saturday: 11 AM – 8 PM; Sunday thru Thursday: 11 AM – 7 PM
📅 Pizzeria: Monday thru Saturday: 12 – 8 PM; Sunday: 12 – 8 PM
📅 Live Music: Andrew Moses on Saturday: 5 – 8 PM
More info: Sorrenti’s Family Estate Winery
Tolino’s Vineyard
📍 Bangor, PA
📅Monday thru Thursday: 12 – 5 PM; Friday: 12 – 8 PM (til September); Saturday: 11 AM – 5 PM; Sunday: 12 – 5 PM
Family Fridays (May to September)
4 – 8 PM
Enjoy live music from 5 – 8 PM and food trucks onsite. Yard games for the kids and a visit from Chill on Wheels, our local ice cream truck.
Food Truck Saturday
12 – 5 PM
(weather depending)
Weekend Music Series
Saturdays and Sundays from 1 – 4 PM
More info: Tolino’s Vineyard
🌟 One of a Kinds
Pocono Organics
📍 Long Pond, PA
📅 Saturday
Farm Tours! Book here: Farm Tour registration
More info: Pocono Organics
📥 Put This In Your Plans!
Pocono Raceway – NASCAR
📍 Long Pond, PA
📅 June 20 – 22
More info: Pocono Raceway – NASCAR Race Weekend
Pocono Music Fest & Performing Arts Camp
📍 Various venues, PA
📅 starting June 29
More info: Pocono Music Festival and Performance Camp
😊 Plan Your Weekend!
The Poconos are buzzing with activities this weekend! Whether you’re a local or just visiting, there’s no shortage of events to enjoy. Remember to check event details and weather updates before heading out.
👉 Tip: Tag me on Instagram @MyPoconoMountainHome if you’re out and about—I’d love to see what you’re up to this weekend!
See you around town!
Meagan Lahey
Your resourceful Pocono Mountains REALTOR® + Community Connector
PS: if you’d like your event featured here, please email me at [email protected] or tag me on Instagram or Facebook @MyPoconoMountainHome or DM me on X @MyPoconoMtnHome!
