Here’s a list of major events happening across the Rogue Valley in May 2025, organized by date. Locations span Medford, Ashland, Central Point, Jacksonville, Grants Pass, Eagle Point, and beyond—so there’s something for everyone!

• Medford Growers & Crafters Market
  When: Thursdays, May 1, 8, 15, 22, 29 (weekly)
  Where: Hawthorne Park, Medford
  Discover fresh produce, handmade crafts, and local artisans every Thursday afternoon. Travel Medford

• Barnstormer’s Spring Market at The Expo
  When: Fri–Sat, May 2–3 (4 pm – 3:30 pm)
  Where: Jackson County Expo (Fairgrounds), Central Point
  A two-day pop-up market featuring vintage finds, boutique gifts, plants, and food trucks. What to do in Southern Oregon

• Ashland / Oregon Fringe Festival
  When: Fri–Sun, May 2–4
  Where: Various venues around Ashland
  Celebrating boundary-pushing theatre, comedy, and performance art. What to do in Southern Oregon

• Madrone Trail May Faire Festival
  When: Sat, May 3, 11 am – 3 pm
  Where: Madrone Trail Public Charter School, Ashland
  Maypole dances, live music, crafts, and country-fair fun for families. What to do in Southern Oregon

• Roam the Rogue Wine Tour
  When: Sat, May 3, 11 am – 5 pm
  Where: Upper Rogue Wine Trail (multiple wineries)
  Self-guided tasting tour across local vineyards and food pairings. What to do in Southern Oregon

• Hearts With a Mission Superhero Run
  When: Sat, May 3, 7:30 am – 12 pm
  Where: Valley of the Rogue State Park, Gold Hill
  5K fun run in costume, supporting local charities. What to do in Southern Oregon

• Medford Major Cornhole Tournament
  When: Fri–Sun, May 24–26
  Where: TBD (Medford)
  West Coast’s must-attend youth cornhole championship. Travel Medford

• Waitress (musical) @ Oregon Cabaret Theatre
  When: Sat, May 31 – Sun, June 15 (varies)
  Where: Oregon Cabaret Theatre, Central Point
  Tony-award–winning musical comedy about pies and second chances. Travel Medford

Mother’s Day Weekend Highlights

• Art in Bloom
  When: Sat–Sun, May 10–11 (Sat 11 am – 5 pm; Sun 11 am – 4 pm)
  Where: Downtown Medford (Vogel Plaza, Craterian, Rogue Gallery, Lithia Commons)
  Two-day spring festival with fine art, horticulture booths, live music, and food. art-in-bloom.comdowntownmedford.org

• Made in Southern Oregon
  When: Sat, May 10, 9 am – 4 pm
  Where: Central Point (venue TBA)
  Showcasing artisans, leatherworkers, wood crafters, food producers, and more. What to do in Southern Oregon

• Rogue Valley Bird Day
  When: Sat, May 10, 8 am – 12 pm
  Where: North Mountain Park, Ashland
  Guided bird walks, educational booths, and family-friendly activities. What to do in Southern Oregon

• Grants Pass Wine Stroll
  When: Sat, May 10, 2 pm – 6 pm
  Where: Downtown Grants Pass
  Sip local wines and sample small bites at shops and tasting rooms. What to do in Southern Oregon

Mid-May to Late-May

• Kids Unlimited Southern Oregon Open (basketball)
  When: Sat–Sun, May 10–11
  Where: Rogue X Community Aquatics & Event Center, Medford
  Youth basketball tournament raising funds for underserved children.

• Legacy Sports “Halloween in May” (softball)
  When: Sat–Sun, May 10–11
  Where: Lithia & Driveway Fields, Medford
  Family-friendly fast-pitch tourney with spooky theme.

• Mud Factor Medford
  When: Sun, May 10, 10 am
  Where: Jackson County Sports Park, Central Point
  5K mud-and-obstacle run—no timing chips, just muddy fun!

• Bike & E-bike Skills Workshop
  When: Wed, May 14, 2 pm – 4:30 pm
  Where: Hunter Park, Ashland
  Hands-on safety drills and riding tips for two-wheelers. Travel Medford

• Wild Rogue Pro Rodeo
  When: Thu–Sat, May 15–17 (doors 6 pm, show 7 pm)
  Where: Jackson County Expo, Central Point (1 Peninger Rd)
  PRCA-sanctioned rodeo with bulls, barrel racing, and more. Oregon Festivals & Events Association

• Third Friday Medford
  When: Fri, May 16, 5 pm – 9 pm
  Where: Downtown Medford
  Art-walk, live music, food vendors, and a silent disco. Travel Medford

• 15th Annual Wood House Farm Festival
  When: Sat–Sun, May 17–18 (9 am – 5 pm)
  Where: Wood House, Eagle Point
  Vintage tractors, farm-fresh produce, history booths, and crafts. Travel Medford

• Polish Festival @ Paschal Winery
  When: Sat, May 17
  Where: Paschal Winery, Jacksonville
  Traditional Polish music, food, and wine tasting. Travel Medford

• Jacksonville Parade of Inns
  When: Sun, May 18
  Where: Historic Jacksonville
  Self-guided walking tour of eight charming inns with special perks. Travel Medford

• Medford Open Streets
  When: Sat, May 31
  Where: Downtown Medford (streets closed to cars)
  Car-free route for walking, biking, and pop-up activities. Travel Medford

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