What to Do in the Poconos!
As May winds down and June begins, the Pocono Mountains and Stroudsburg area are buzzing with exciting events. Whether you’re into live music, community festivals, or cultural experiences, there’s something for everyone this weekend. Here’s your curated guide!
🛍️ 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
West End Fireman’s Festival
📍 West End Fairgrounds, Gilbert
📅 Thursday, Friday, Saturday: May 29 – 31, 2025 from 5 – 10:30 PM
Live music, bingo, games, rides and food brings the community together to support Blue Ridge Hook & Ladder, Polk Township, Kunkletown, and West End Volunteer Fire Departments
Touch-A-Truck on Saturday, May 31st from 3 – 5 PM.
Candy Drop on Saturday, May 31st at 5 PM
More info: What to Expect at the West End Fireman’s Festival by WNEP
Pocono Pride Festival
📍 Courthouse Square, Downtown Stroudsburg
🗓️ Sunday, June 1, 12 PM – 5 PM
Live entertainment, food and craft vendors, and performances.
✨ Special Weekend Events
Youth Plein Air Workshop
📍 Quiet Valley Living Historical Farm – Stroudsburg
📅 Saturday, May 31, June 7 and June 14, 2025 – 9:30 AM to 12:30 PM
Hands-on experience for young artists to learn essential techniques in drawing, color theory, and various painting media, all while working outdoors on the farm.
More info: Quiet Valley Living Historic Farm – Plein Air Event
Grand Opening! The Liberty Tree Ranch!
📍 The Liberty Tree Ranch – East Stroudsburg
📅 Saturday, May 31, 2025 – 11 AM to 2 PM
Founded by a Veteran of the Global War on Terror, and his family, embrace the pioneering spirit through hands-on agritourism that honors sustainability, education, and family values!
More info: The Liberty Tree Ranch
Indoor Artisan Crafters Market
📍 Wonderland Madhouse – The Crossings Outlets, Tannersville
📅 Saturday, May 31, 2025 from 1 – 5 PM
More info: Wonderland Madhouse Facebook Event
Events at the “Main Street Makery”
📍 Main Street – Stroudsburg
📅 Saturday, May 31, 2025
10:30 AM: Slime Making
12 PM: Junior Cookie Decorating
1 PM: Candle Making
3 PM: Ravioli Making (sold out)
Tickets: Main Street Makery Events
Used Book Sale
📍 Hughes Library – Stroudsburg
📅 Saturday, May 31, 2025 – 9 AM to 4 PM and Sunday, June 1 – 12 – 4 PM
More info: Eastern Monroe Public Library Book Sale
Zip, Zoom & Bloom
📍 Camelback Resort – Tannersville
📅 Saturday, May 31, 2025 – 12 to 4 PM
More info: Camelback Resort Adventures
Paint and Sip
📍 Creative Canvas Studio – Stroudsburg
📅 Saturday, May 31, 2025 – 6 – 9 PM
More info: Creative Canvas Studio
3rd Annual Ribbon Run
📍 Mountain View Vineyard – Stroudsburg
📅 Sunday, June 1, 2025 – 10 AM – 5 PM
For survivors and their family & friends, to support each other and to raise funds for patients’ needs not covered by insurance. Also, local craft vendors, food trucks, and a cash bar are available.
More info: Mountain View Vineyard
Ride for a Cure
📍 Pocono Mountain Harley Davidson – Tannersville
📅 Sunday, June 1, 2025 – 10 AM
More info: Pocono Mountain Harley Davidson
Celtic Wood & Wires Concert
📍 Columcille Megalith Park– Bangor
📅 Sunday, June 1, 2025 – 2 to 4 PM
More info: Columcille Megalith Park
🎶 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
Sarah Street Grill – Stroudsburg
📅 Sunday, June 1, 2025 at 8:30 – 11:30 PM
📍 Sarah Street, Downtown Stroudsburg
Lady King & The Aces
More info: Sarah Street Grill
Stonehaus Meadery – Stroudsburg
📅 Saturday, May 31, 2025 at 8 – 11 PM
📍 Main Street, Downtown Stroudsburg
Tom Riccobono
More info: Stonehaus Meadery
🌿 Outdoor Adventures
Hickory Run State Park
📍 White Haven, PA
Explore the 15,990-acre park in the western foothills of the Pocono Mountains. This large park has more than 40 miles of hiking trails, three state park natural areas, miles and miles of trout streams and a Boulder Field in the middle of a forest!
More info: Hickory Run State Park
Spring Zing “Pollinator” Pull and Races
📍 Mahoning Valley Speedway, Lehighton, PA
📅 Saturday, May 31, 2025 at 4 PM
Modified 50 Lap, Street Stock, Hobby Stock and Pro 4 races. It’s also Pocono Raceway night with ticket giveaways and Pace Car will be on display!
More info: Mahoning Valley Speedway
🚂 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
📅 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
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
The Underground Experience
Saturday and Sunday – 2PM
*Reservations: Eventbrite Tickets
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
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
Sunday Afternoon Music
Sunday, May 18, 2025 at 1 – 4 PM
3rd Annual 5K Ribbon Run
Sunday, June 1, 2025 at 10 AM
For survivors and their family & friends, to support each other and to raise funds for patients’ needs not covered by insurance. Also, local craft vendors, food trucks, and a cash bar available.
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
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
Charcuterie Workshop with Gather & Graze
Sunday, June 1, 2025 at 2 PM – 3 PM
Tickets: Charcuterie Workshop
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!
Greek Fest of the Poconos
📍 Holy Cross Greek Orthodox Church, Stroudsburg, PA
📅 starting June 5 – 8 at 4 PM
More info: Greek Fest!
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!
Whether you’re looking to enjoy live music, celebrate community, indulge in fine wines, or embark on a state park adventure, the Stroudsburg area has something special for you this weekend. Don’t miss out on these exciting events!
👉 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!
