May is when the Sullivan Catskills truly wake up—lush greenery returns, lake days begin, and the calendar fills with live music, markets, and can’t-miss seasonal events. Whether you’re planning a quiet retreat or a weekend full of exploring, there’s something happening around every corner.

Here’s your curated guide to May events in Sullivan County + nearby areas for a dreamy spring escape.

🌸 Spring Reopening Season at Bethel Woods Center for the Arts

One of the most iconic destinations in the region officially kicks off its spring season in May.

May 1: Grounds + exhibits reopen
May 6: Golf cart tours begin
Ongoing: Museum open daily

📸 Digital Photography Course (May Sessions Continue)

Tap into your creative side with hands-on learning surrounded by nature at Bethel Woods Center for the Arts.

🎨 Historic Site Tours (Beginning May 8)

Step into music history with guided tours of the original Woodstock grounds—equal parts educational and nostalgic.

✨ Casskell tip: Pair this with a scenic drive or picnic after.

🎶 Jazz at Lincoln Center (May 3)

Held at Bethel Woods Center for the Arts, this intimate performance blends timeless jazz with a relaxed Catskills atmosphere—perfect for a cozy date night or solo escape.

🎤 Pavilion Concert Season Begins (Late May)

Outdoor concerts return in full force—don’t miss:

HARDY: The Country Tour — May 30

Concert season here is a summer staple, with shows continuing all season long.

🌿 Nature & Slow Spring Moments

Wings of Spring — Guided Birdwatching Walk

📅 May 2 | 9:00 AM – 11:00 AM
📍 Flying Trillium Gardens & Preserve

A peaceful way to welcome the season—wander the Neversink Watershed while spotting migratory birds and soaking in the quiet beauty of early spring.

🌱Community Events, Markets & Pop-Ups

Maple Woods Farm Stand Opening

📅 May 1 | 1:00 PM – 6:00 PM
Seasonal farm stand favorites return—fresh, local, and the perfect first stop for your weekend provisions.

Cinco de Mayo Festival — Liberty

📅 May 2 | 10:00 AM – 4:00 PM
Celebrate culture, community, and tradition in downtown Liberty with food, music, and festive energy.

Lego Show — Jeffersonville

📅 May 9 | 10:00 AM – 2:00 PM
A fun, family-friendly event featuring impressive builds, hands-on activities, and interactive exhibits.

14th Annual Angler’s Market — Roscoe

📅 May 23 | 10:00 AM – 3:00 PM
Hosted by the Roscoe Chamber of Commerce, this beloved local event is a must for fishing enthusiasts and curious visitors alike.

Callicoon Farmers Market (Every Sunday)

📅 Sundays | 11:00 AM – 2:00 PM
A staple of the season—browse local farms, baked goods, artisan products, wine, cider, and more in the heart of Callicoon.

✨ Casskell tip: Make this part of your Sunday ritual—coffee, slow browsing, and a scenic Delaware River stroll after.

🧘‍♀️ Cozy & Creative Weekly Rituals

Ratty Books Story Club

📅 Mondays & Saturdays | 10:00 AM – 12:00 PM
A sweet, welcoming space for kids of all ages—stories begin at 10:15, with a relaxed and cozy atmosphere.

Sunday Morning Knitting Circle — Roscoe

📅 Sundays | 9:00 AM – 12:00 PM
Bring your current project and settle in for a few hours of crafting, coffee, and community. All crafts welcome.

Pilates at Bodies + Plants

📅 Sundays | 9:45 AM + 11:00 AM
Small group reformer and springboard classes—perfect for a slow, mindful start to your Sunday.

🎶 Food, Music & Nightlife

The Big Tasty Kitchen Takeover — Cochecton

📅 May 5 | 3:00 PM – 7:00 PM
Celebrate Cinco de Mayo with bold flavors and a special firehouse kitchen takeover—casual, fun, and full of personality.

Karaoke Nights at Van Smokey

📅 Fridays | 9:00 PM – Late
A lively late-night option—perfect if you’re in the mood for something spontaneous and a little nostalgic.

Live Music: Mikel Paris at Big Eddy Brewing Co.

📅 May 22 | 7:00 PM – 10:00 PM
An energetic, free live show paired with craft brews—ideal for a relaxed but vibrant night out.

🌷 Worth the Drive

Albany Tulip Festival

📅 May 9-10 Perfect for a mothers day outing!

If you’re up for a scenic day trip, this iconic festival features:

Over 100,000 blooming tulips
Live music + food vendors
Artisan markets

A dreamy, colorful way to celebrate spring at its peak.

🌼 Local Markets, Pop-Ups & Community Events

Throughout May, Sullivan County hosts a rotating mix of:

Farmers markets reopening for the season
Local artisan pop-ups
Live music nights at restaurants and small venues
Book clubs, workshops, and creative gatherings

There’s almost always something happening—this region thrives on community-centered events and spontaneous moments.

✨ Casskell tip: Ask your host or check local boards—you’ll often find hidden gems not widely advertised.

🌿 Plan Your Perfect May Stay

May is that sweet spot—before summer crowds arrive but after everything begins to bloom. Whether you’re here for an event or simply the atmosphere, the Sullivan Catskills in May feel like a quiet kind of magic.

🌿 May in the Sullivan Catskills: Events Worth Planning Your Getaway Around