Things to Do in Medford Oregon (May 2026): Top Events, Festivals & Local Activities
If you’re looking for things to do in Medford Oregon this May, you’re in one of the best months of the year to get out and experience everything Southern Oregon has to offer.
From wine tours and festivals to live music and family-friendly events, May is packed with reasons to explore the area. Whether you’ve lived here for years or you’re just getting familiar with Medford, these are the events people look forward to every spring.
🎭 Oregon Shakespeare Festival (All Month)
Oregon Shakespeare Festival
Running throughout May just minutes from Medford, this nationally recognized festival brings in top-tier performances ranging from Shakespeare classics to modern productions.
It’s one of the biggest cultural draws in the region and a big reason why people love living in the Rogue Valley.
🌸 Art In Bloom Festival (May 9–10)
A spring favorite featuring floral displays, local artists, and community exhibits.
It’s a great weekend event if you’re looking for something relaxed, creative, and easy to enjoy with family or friends.
🍷 Spring Uncorked Wine Tour (May 16)
Southern Oregon’s wine scene is on full display here. Local wineries open their doors for tastings, special releases, and scenic vineyard experiences.
If you’ve never explored the wineries around Medford, this is one of the best times to do it.
🤠 Wild Rogue Pro Rodeo (May 14–16)
A high-energy event that brings together rodeo competitions, food vendors, and live entertainment.
It’s a staple in Southern Oregon and always draws a strong crowd.
🎉 Rogue Comic Con (May 16–17 & May 23–24)
One of the fastest-growing events in the area, featuring vendors, entertainment, and a mix of indoor activities that make it perfect for all ages.
🎨 Clayfolk Spring Show & Sale (May 9–10)
Local artists showcase handmade ceramics and artwork, giving you a chance to support the creative community while finding unique pieces.
🌿 Wood House Farm Festival (May 16–17)
A laid-back outdoor event with vendors, food, and activities in a farm setting.
Perfect if you’re looking for a slower-paced weekend with a strong local feel.
🏇 Kentucky Derby Party @ Ravissant Cellars (May 2)
A fun mix of wine, social atmosphere, and Derby-themed celebration to kick off the month.
🎶 Live Music & Concerts (All Month)
There’s no shortage of live music throughout May, from local bands to larger performances at venues like The Holly Theatre and local wineries and breweries.
⚾ Medford Rogues Baseball Games (Late May)
Baseball season starts up again, offering an easy, family-friendly way to spend an evening.
Why May Is One of the Best Times to Be in Medford
May brings together everything people enjoy about living here:
- Comfortable weather and longer days
- A full calendar of events and activities
- Strong local energy across Medford, Ashland, and Jacksonville
- Easy access to wineries, outdoor spaces, and entertainment
It’s the kind of month that reminds you why Southern Oregon is such a desirable place to live.
❓ FAQs
What are the best things to do in Medford Oregon in May?
Some of the top events include the Oregon Shakespeare Festival, Spring Uncorked Wine Tour, Wild Rogue Pro Rodeo, Rogue Comic Con, and Art In Bloom Festival.
Are there family-friendly events in Medford in May?
Yes. Events like Art In Bloom, Wood House Farm Festival, and Medford Rogues games are great options for families.
What wine events are happening in Medford Oregon?
Spring Uncorked is one of the biggest wine events of the month, along with ongoing tastings at local vineyards.
Is May a good time to visit or explore Medford Oregon?
Yes. The weather is ideal, events are in full swing, and it’s one of the most active times of year in the area.
What is happening in Medford Oregon this weekend?
Most weekends in May include a mix of festivals, live music, markets, and local events across the Rogue Valley.
Thinking About Your Next Move in Southern Oregon?
Whether you’re enjoying everything Medford has to offer, thinking about selling, or curious what your home might be worth in today’s market, timing and local insight matter.
You can explore available homes, check your home value, or connect with a local expert here:
👉 Rockwell Group
