What’s Happening in Southern Oregon: Your Guide to Events (March 24 – April 5, 2026)

Spring is officially unfolding in the Rogue Valley, and the calendar is packed! Whether you’re looking to settle into a theater seat at the world-renowned Oregon Shakespeare Festival, hunt for Easter eggs (for kids and adults!), or sip your way through the Bear Creek Wine Trail, Southern Oregon is the place to be over the next two weeks.

At Rockwell Group, we love seeing our community thrive. Here is your curated guide to the best local events in Medford, Ashland, Jacksonville, and beyond.

🎭 Arts & Culture

Oregon Shakespeare Festival (OSF) | Ashland

The 2026 season is in full swing at the Angus Bowmer Theatre. Don’t miss these world-class productions:

  • A Raisin in the Sun: A fierce and tender revival of Lorraine Hansberry’s seminal work.

    • Dates: March 24, 27, 29; April 1, 3, 4.

  • Come From Away: The Tony-winning musical about the power of community in the wake of 9/11.

    • Dates: March 25, 28; April 2, 3.

  • A Midsummer Night’s Dream: Shakespeare’s classic comedy gets a magical, musical update.

Drum Tao | Medford

Thursday, April 2 | 7:00 PM | Craterian Theater

Experience the thunderous power of Japanese Taiko drumming. This internationally-renowned troupe combines athletic precision with dazzling visuals and costumes.

🍷 Wine & Dine

2nd Annual Bear Creek Wine Trail Festival

Saturday, March 28 | Belle Fiore Winery, Ashland

Choose between two sessions (12:00–2:30 PM or 3:30–6:00 PM) to taste the best of the region. Tickets include seven samples and a one-year wine trail passport!

Cork 'N' Fork @ Paschal Winery | Talent

Wednesdays, March 25 & April 1 | 6:30 PM

  • Mar 25: Chicken Meatballs & Penne by Aga & Rory.

  • Apr 1: Herb Roasted Chicken by Chef James Jones.

  • Note: Reservations required (541-535-7957).

Oysters & Ales @ Bella Union | Jacksonville

Thursdays, March 26 & April 2 | 6:00 PM – 8:00 PM

A 28-year tradition! Enjoy fresh oysters paired with a different featured brewery each week.

👨‍👩-👧‍👦 Family & Community

2026 ACCESS Senior Fair | Medford

Tuesday, March 24 | 9:00 AM – 3:00 PM | Rogue X

A free event connecting seniors and families with healthcare, financial planning, and social resources. Donations for food pantries are welcome.

Hero Day | Children’s Museum of Southern Oregon

Sunday, March 29 | 12:00 PM – 5:00 PM

Kids can meet local firefighters and police officers, explore emergency vehicles, and learn about the heroes in our community.

Animal Encounters: BUGS-R-US | Medford

Saturday, April 4 | 11:00 AM | Children’s Museum of Southern Oregon

Get up close and personal with the "Bug Zoo." Learn about habitats and even hold a bug if you're brave enough!

🐣 Easter Egg Hunts & Spring Fun

Event Location Date/Time Highlights
Easter Eggstravaganza Donahue Frohnmayer Park Mar 29, 10:30 AM Games, prizes, and a petting zoo.
Easter Candy Stroll Medford Center Apr 4, 12:00 PM Pick up a stamp card near Firehouse Subs.
Adult Easter Egg Hunt Hummingbird Estate Apr 4, 11:00 AM 21+ only. Prizes include wine and stays at the inn!
5th Annual Egg Hunt Vista 222, Grants Pass Apr 4, 12:00 PM Food trucks, live music, and face painting.

🎸 Live Music & Nightlife

  • Trivia Night: Tuesdays (Mar 24 & 31) @ The Copper Plank, Medford (6:00 PM).

  • Traditional Irish Music: Thursdays (Mar 26 & Apr 2) @ Dunbar Farms (5:30 PM).

  • Blue Lightning: Friday, March 27 @ RoxyAnn Winery (6:00 PM).

  • Danielle Kelly Soul Project: Saturday, March 28 @ Rellik Winery (6:00 PM).

  • St. Paul & The Broken Bones: Sunday, March 29 @ The Holly Theatre (8:00 PM).

  • 90s Night with Aaron Reed & Adam Gabriel: Friday, April 3 @ The Copper Plank (8:00 PM).

Why Southern Oregon?

From the world-class theater in Ashland to the rolling vineyards of Central Point and Medford, Southern Oregon offers a lifestyle that balances culture with the great outdoors.

Are you looking to move closer to the action? Whether you want a home within walking distance of the Oregon Shakespeare Festival or a quiet vineyard estate, Rockwell Group is here to help you navigate the Southern Oregon real estate market.

Let’s Chat!

  • Which of these events are you most excited about?

  • Do you prefer the local wine scene or the live theater productions?

  • Would you like a personalized list of homes currently for sale near these event hotspots?

Contact Rockwell Group Today to Start Your Home Search!

Disclaimer: Rockwell Group is not the host or owner of these events. This list is provided for informational purposes only. Event details, times, and availability are subject to change by the organizers. We recommend verifying details via the provided links before attending.