What to Do in the Poconos!
Hey there, weekend wanderers! 🌞 Ready to dive into a delightful mix of festivities, flavors, and fun? Whether you’re a local or just passing through, the Poconos region is buzzing with events that’ll make your weekend unforgettable. Let’s explore what’s happening from May 16 to 18!
🛍️ 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
Pocono Farmers Market
📍 Blakeslee (115 south of 80)
📅 Saturday, May 17 – 7:30 AM to 4 PM
Blue Ridge Flea Market
📍 Saylorsburg (648 Route 115)
📅 Saturday, May 17 & 18 – 6:30 AM to 3 PM
More info: Blue Ridge Flea Market
✨ Special Weekend Events
Herb Pairing Workshop
📍 That Planty Chick – Sciota
📅 Friday, May 16 and Saturday, May 17 – 1 to 3 PM
Learn what herbs work together!
More info: That Planty Chick
Dine for the Parks Fundraiser
📍 Stroud Rec – Bartonsville
📅 Friday, May 16 – 5 to 9 PM
Mention the fundraiser to your server to help Friends of the Stroud Region Open Space & Recreation Commission!
More info: Stroud Rec
May Movie Nights
📍 First Baptist Church – East Stroudsburg
📅 Friday, May 16 – 8 to 10 PM
Friday family movie nights! Bring a lawn chair or blanket. Popcorn and a drink will be provided for everyone!
More info: Friday Family Movie Nights
Coffee With A Cop
📍 Pocono Twp PD – hosted at Jiva Java in Bartonsville
📅 Saturday, May 17 – 9 AM to 12 PM
Meet your local Police Officers and grab a coffee!
More info: Pocono Twp Police Department and Jiva Java
Sip Along the Strip
📍 Zinc City Motorcycle Club, Kresgeville
📅 Saturday, May 17 – noon to 5 PM
Sample wines, brews, and spirits from local businesses. There will also be food trucks, music and many vendors for you to “shop small”. Must be 21+ years old.
Facebook Event: Sip Along the Strip 2025
Lodge Hall Open House
📍 Polk Twp Historical Society – 104 Lodge Hall Rd Kresgeville
📅 Sunday, May 18 – 10 AM to 3 PM
Get a glimpse into Lodge Hall. Built in 1888.
Haircuts for Heroes
📍 American Legion #346 – East Stroudsburg
📅 Sunday, May 18 – 11 AM to 2 PM
For Veterans and Members. Call/text or email Tim at 570-994-5657 or [email protected]
Support the Blue Ride
📍 Three6Nine LE/MC Pocono Chapter – Easton
📅 Saturday, May 17 – 10:30 AM registration; Kickstands up at noon
Scenic escorted ride to support our Police Officers. Meet at Famous Smoke Shop at 90 Mort Dr, Easton PA. Tix $25 rider; $15 passenger. Food available from “You Got Pork’d”.
More info: Support the Blue Ride
🎉 Festivals & Celebrations
Happy Hour Street Festival
📍 Happy Hour Bar & Grill
📅 Saturday, May 17
Kick off your weekend with a bang at this vibrant festival. Expect a day filled with live music, delectable food, and a lively atmosphere that’s perfect for friends and families alike.
More info: Happy Hour Bar & Grill
Jim Thorpe’s 138th Birthday Celebration
📍 Jim Thorpe, PA
📅 Saturday, May 17
Join the town in honoring its namesake, the legendary athlete Jim Thorpe. The celebration includes a Native American Festival, lectures, vendors, and more. It’s a cultural experience you won’t want to miss.
More info: Jim Thorpe’s 138th Birthday Celebration
Quiet Valley’s Annual Farm Animal Frolic
📍 Quiet Valley Living Historical Farm
📅 Saturday & Sunday, May 17–18
Experience the joys of spring on the farm! Meet baby animals, enjoy traditional crafts, and immerse yourself in farm life from days gone by. It’s a delightful outing for all ages.
More info: Quiet Valley Historic Farm
8th Annual Wine & Song Festival
📍 Blue Ridge Estate Vineyard & Winery, Saylorsburg, PA
📅 Saturday, May 17 – 1 to 6 PM (FREE)
It’s a day of listening pleasure, great wine, food trucks and more!
Here’s this year’s lineup!!
1:00-2:00 pm Andrew Moses
2:15-3:15 pm Hannah Violet
3:30-4:30 pm Ian Kirk
4:45-6:00 pm Littlebird & the bad eggs
This is a Free Event! No reservations needed!
Facebook Event: 8th Annual Wine and Song Festival
🎶 Live Music & Entertainment
🗓️ All Weekend
Music on Main – Stroudsburg
🕕 6:00–9:00 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
🌿 Outdoor Adventures
Big Pocono State Park – Climb to Conquer Cancer Pocono
📍 Tannersville, PA
📅 Saturday, May 17th, 2025 – 8 AM
Hosted by: American Cancer Society
https://secure.acsevents.org/site/TR/DetermiNation/CFPCY25NER?pg=entry&fr_id=110865
Embrace the great outdoors and raise money with a hike through Big Pocono State Park. Trails offer panoramic views and diverse terrains. It’s a haven for nature enthusiasts!
More info: Climb to Conquer Cancer Poconos
🚂 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.
More info: Ride a Bike on the Rails
🍷 Wineries and Vineyards
Blue Ridge Estate Vineyard & Winery
📍 Saylorsburg, PA
📅 Friday, Saturday, and Sunday
Many events throughout the year including Barrel Tasting, Underground Dinner Experience, Murder Mysteries, Charcuterie Workshops 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
8th Annual Wine and Song Festival*
Saturday, May 17th – 1pm-6pm
*Free event, no reservations needed
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
More info: Blue Ridge Estate Vineyard & Winery
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
Sunday, May 18th, 2025 from 12:30 – 3 PM
More info: Indo-Chinese Food and Wine Pairing Event
Mountain View Vineyard, Winery, Brewery & Distillery
📍 Stroudsburg, PA
📅 Saturday, and Sunday
JEEP Go Topless
Saturday, May 17th, 2025 at 10 AM
Food trucks, DJ Jon, axe throwing and Jeep Juice! What else do you need?
Live music with Chris Zelenka
Sunday, May 18, 2025 at 1 – 4 PM
Wheel ‘n Wine
Sunday, May 18, 2025 at 3 – 5 PM
Children 8+ can register with the registration of an adult to make a pot on the pottery wheel while the adults sip their favorite wine! Text or call 610-823-3742 for questions, the link to register is below:
Wheel ‘n Wine registration
More info: Mountain View Vineyard
Sorrenti’s Family Estate
📍 Stroudsburg, PA
📅 Saturday, and Sunday
Live Music with Chris Colaiaco
Saturday, May 17th, 2025 at 5 – 8 PM
Live Music with Stan & Elise
Sunday, May 18th, 2025 at 1 – 4 PM
More info: Sorrenti’s Family Estate Winery
Tolino’s Vineyard
📍 Bangor, PA
📅 Friday, Saturday, and Sunday
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
Saturday, May 17th, 2025 at 12 – 5 PM
JT Grills Food Truck Onsite (weather depending)
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
Greek Fest of the Poconos
📍 Holy Cross Greek Orthodox Church, Stroudsburg, PA
📅 starting June 5 – 8 at 4 PM
More info: Greek Fest!
😊 Final Thoughts
That’s your weekend snapshot, friends! Whether you’re enjoying live music, savoring something delicious from a food truck, or catching a free film, the Pocono Mountains always have something happening.
👉 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
Here’s your HEYZINE link of this weekend’s events: May 16 -18, 2025: Events in the Pocono Mountains
PS: if you’d like your event featured here, then please email me at [email protected] or tag me on Instagram, Facebook @MyPoconoMountainHome or DM me on X @MyPoconoMtnHome!
