Events

All Day

July 4th Weekend Fun!

To Be Announced Event Schedule...   Join us for tons of Patriotic Resort Fun all weekend long. Including: cocktail making classes, tie dye, pool parties, corn hole tournaments, slushies, popsicles, oyster shucking classes, s'mores and so much more!

Hiking Excursion

This Saturday, experience some of the best that the Catskills have to offer on an adventure with Upstate Hiking. Your licensed guide & adventure photographer will lead you into the […]

Meditation Workshop w/ Sarah Mirsini

Reconnect, reset, and find your center in this guided meditation workshop led by Sarah Mirsini. Set in the peaceful surroundings of the mountains, this immersive experience is designed to help […]

Pickleball Clinic With Cathy

Ready to up your pickleball game? Join Cathy for an energetic and fun-filled clinic designed for players of all levels! Whether you’re a beginner looking to learn the basics or […]

Tiki Bar + BBQ

Get ready for a taste of island vibes with a mountain twist at Wylder’s Tiki Bar & BBQ! Enjoy delicious smoky barbecue favorites alongside refreshing tropical-inspired drinks, all set against […]

Wyld Mini Carnival @ The Yard

Kick off the holiday weekend with a fantastic day of carnival fun at Wylder Windham In our Yard! Enjoy classic games like: Dart Soccer Ring Toss Basketball Toss Can Smash And yes... a Dunk Tank – and so much more! Bring your friends and family and get ready for an afternoon full of laughter, games, and great memories. See you […]

Recurring

Live Local Music – Saturdays 1-3pm

Tickler's Crab Shack & Restaurant 21551-A Chesapeake House Drive, Tilghman

Join us weekly for Live Local Musicians playing at tickler's Crab Shack on the Water from 1-3pm   Make a Dining Reservation through our Dining page or Resy

Pop in, Pop Out Shop Local: Cosmo Cowgirl Charm Bar

Stop by the Main Lodge between 2PM-7PM and shop Cosmo Cowgirl Charm Bar Custom. Tarnish-Free. Affordable. We believe that tarnish-free, charm jewelry should be accessible to everyone, merging personal style with affordability. Open to all and community guests!  Location: @ the Main Lodge

Recurring

Oyster Shucking Class & Demo

Join us at the Shack from 3-4pm every Saturday to learn all about Oysters. Learn how to shuck them and even get to taste these amazing bivalves.

Balloon Twisting with Crazy Christine

Looking for a little extra fun during your stay? Stop by and watch Crazy Christine work her magic with balloons! Full of color, energy, and surprises! Starting at 5pm and ending at 6pm.

Hatchet Throwing In Killside

Unleash your inner lumberjack with hatchet throwing at Wylder! Whether you’re a first-timer or a seasoned pro, this thrilling activity offers a unique way to challenge your aim and have a blast outdoors. Perfect for friends, families, or team-building—step up, take your shot, and see if you’ve got what it takes to hit the bullseye. […]

Equilibrium Beer Tasting

Discover the bold and innovative flavors of Equilibrium Brewing at our exclusive beer tasting event. Sample a curated selection of their finest brews, crafted with passion and creativity. Whether you're a seasoned beer lover or new to craft brewing, this tasting offers a perfect chance to explore unique styles and learn more about the brewing […]

The Knitting Room @ Wylder Workshop

Always wanted to learn how to knit? Come in as an absolute beginner and learn to make your very first chunky hat or scarf! You will receive a pattern and yarn, and we will teach you how to read a pattern, cast on, make the Knit stitch, and knit flat or in the round. Suitable […]

Recurring

Sunset Cruises

Come cruise the Bay and its tributaries on a Classic Chesapeake Bay Charter Fishing Boat. The best way to explore the Shore is by water. You'll see plentiful amounts of nature, beautiful waterfront homes, the famous Tilghman Drawbridge and so much more! Cruises are from 6-8pm Cruises are $65 a person regardless of age.   […]

$65
Recurring

Magic Show

Tickler's Crab Shack & Restaurant 21551-A Chesapeake House Drive, Tilghman

Join Local Magician John Dodge for a night of fun!   Family friendly and all are welcome!   6-7pm Table-side Magic for dining guests at Tickler's 7-8pm Magic show in the Ballroom  

Textured Paint & Sip W/ Handmade Haven

Unleash your creativity in this unique Textured Paint & Sip experience with Handmade Haven! Enjoy a relaxing atmosphere where you can sip your favorite beverage while learning to create beautiful textured artwork step-by-step. Perfect for artists of all skill levels, this hands-on workshop combines artistic fun with good company and plenty of inspiration. Come ready […]

Live Music Feat Joseph James & Friends @ Babblers Patio

Kick back and soak up the sounds of summer with Joseph James & Friends live on Babblers Patio! Enjoy an evening of soulful tunes, great vibes, and good company under the open sky. Whether you're here for a relaxing night out or a fun-filled gathering with friends, this is the perfect soundtrack to your day. […]

Cutest Dog Contest @ Killside

Bring your furry friend and show off their charm at Wylder’s Cutest Dog Contest! Whether your pup is a fluffy cuddle bug or a playful goofball, this fun and friendly competition is all about celebrating the lovable personalities of our four-legged guests. Prizes, tail wags, and lots of smiles guaranteed. Come join the fun and […]

Magic on Main W/ Sean Doolan

Prepare to be amazed as Sean Doolan brings his captivating magic show right to the heart of Wylder! With mind-bending illusions, jaw-dropping sleight of hand, and a touch of charm, Sean’s performance is perfect for all ages. Whether you’re a magic enthusiast or just looking for a fun night out, this show promises wonder, laughter, […]

Karaoke In The Rec Room

Grab the mic and show off your star power at Karaoke night in The Recreation Room! Whether you’re belting out your favorite hits or cheering on friends, this is the perfect spot to let loose, have fun, and create unforgettable memories. Great tunes, good vibes, and plenty of laughs guaranteed—come ready to sing your heart […]