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Events and things to do in May 2026 in Windsor California

Things to Do in Windsor CA – May 2026 | Events Calendar
Windsor, California

Things to Do in May 2026

Your complete guide to events, festivals, wineries, parks, races & more in Windsor, CA — all in chronological order.

May is one of the best months to be in Windsor. The Sonoma County wine country greens up, race season kicks off on the Town Green, the Farmers Market hums every Sunday, and community celebrations fill the calendar from the first weekend to Memorial Day weekend. Here’s everything happening in Windsor this May 2026.

Dates and times are subject to change. Always confirm details with the event organizer before heading out.

May 2026 Events Calendar

Week 1 — May 1–3
1
Fri
May
CommunityFundraiser
Make Kids Smile Murder Mystery Masquerade Fundraiser
📅 Friday, May 1, 2026 📍 Windsor, CA
PDI Surgery Center hosts a fun-filled murder mystery masquerade fundraiser benefiting their Make Kids Smile charitable program. A great evening out for a great cause.
Event Details
2
Sat
May
CommunityGardening
Food For Thought Plant Sale & Garden Tour
📅 Saturday, May 2, 2026 📍 Windsor, CA
Shop a wonderful variety of veggie, herb, and flower starts to bring home — all proceeds benefit the Food For Thought food bank. A beloved annual community event for gardeners of all levels.
Event Details
3
Sun
May
RaceFamilyOutdoors
Sonoma County Balloon Chase 5K & Little Chasers 1K
📅 Sunday, May 3, 2026 — 8:00 AM 📍 Keiser Community Park, Windsor
The inaugural Sonoma County Hot Air Balloon Classic 5K winds through the scenic Starr Road and Windsor River Road corridors. All runners get a hat and collectible balloon pin. Kids can join the 1K Little Chasers Dash. Strollers welcome. Photo ops with real hot air balloons included with registration!
Register & Details
Week 2 — May 4–10
5
Tue
May
FestivalFreeCultural
Cinco de Mayo Festival at Windsor Palms Plaza
📅 Tuesday, May 5, 2026 — 2:00–8:00 PM 📍 Windsor Palms Plaza, 8465 Old Redwood Hwy, Windsor
The Town of Windsor brings authentic Mexican cuisine, live music, traditional folklorico dance performances, and family-friendly activities to Windsor Palms Plaza. Free admission. One of the most festive evenings of the spring.
Windsor Chamber Calendar
5
Tue
May
NetworkingWomen
Sonoma County Women Professionals (SCWP) Luncheon
📅 Tuesday, May 5, 2026 📍 Windsor, CA
A monthly networking luncheon for professional women in Sonoma County, hosted through the Windsor Chamber. Registration required.
Register & Details
6
Wed
May
Parks & RecFreeKids
Rec Party in the Park — Starr Creek Park
📅 Wednesday, May 6, 2026 — 4:30–6:00 PM 📍 Starr Creek Park, Windsor
Part of the Town of Windsor’s free Spring 2026 Rec Party series. All ages welcome for relay races, lawn games, water activities, sports challenges, raffle giveaways, and the crowd-favorite Adults vs. Kids Dodgeball finale.
Town Calendar
9
Sat
May
ArtsCulturalFestival
Native Arts Festival — Windsor Town Green
📅 Saturday, May 9, 2026 — 11:00 AM–4:00 PM 📍 Windsor Town Green, 701 McClelland Dr, Windsor
The Progressive Tribal Alliance presents the Third Annual Native Arts Festival — the largest event of its kind in Sonoma County. Enjoy Pomo dancers, Native artists and vendors, traditional food, a Kid Zone, scavenger hunt, songs, blessings, and raffle. Free shuttle from Windsor High School. An unforgettable community celebration.
Event Info
10
Sun
May
HolidayFamily
Mother’s Day — Special Market Celebration
📅 Sunday, May 10, 2026 — 9:00 AM–12:30 PM 📍 Windsor Town Green (Farmers Market)
Celebrate Mom at the Windsor Certified Farmers Market! The market’s beloved Mother’s Day tradition includes special programming — moms and grandmas enjoy tea, kids can make flower arrangements to take home, and the whole family can browse fresh local produce, flowers, artisan goods, and more.
Farmers Market Calendar
Week 3 — May 11–17
13
Wed
May
Parks & RecFreeKids
Rec Party in the Park — Robbins Park
📅 Wednesday, May 13, 2026 — 4:30–6:00 PM 📍 Robbins Park, Windsor
The final stop in the Spring 2026 Rec Party series. Free family fun with relay races, lawn games, water activities, raffle prizes, and Adults vs. Kids Dodgeball. All ages welcome — no registration required.
Town Calendar
15
Fri
May
Arts & CraftsWorkshop
Sit and Sew with a Pro
📅 Friday, May 15, 2026 📍 Windsor, CA
A hands-on sewing workshop with a professional instructor in Windsor. Great for all skill levels — bring a project or learn something new in a welcoming, creative setting.
Find on Eventbrite
16
Sat
May
RaceHalf Marathon5K
Windsor Half Marathon, 10K & 5K
📅 Saturday, May 16, 2026 — 7:30 AM 📍 Windsor Town Green, Windsor
One of Sonoma County’s most beloved road races, starting and finishing on the iconic Windsor Town Green. Choose from the half marathon, 10K, or 5K distances and run through the rolling wine country roads surrounding Windsor. A must-do for local runners.
Event Info
20
Wed
May
GovernmentCivic
Town Council Regular Meeting
📅 Wednesday, May 20, 2026 — 6:00 PM 📍 Civic Center Council Chambers, 9291 Old Redwood Hwy, Bldg 400, Windsor
The Windsor Town Council meets the 1st and 3rd Wednesday of each month. Meetings are open to the public and broadcast live on Comcast Ch. 27 and AT&T U-verse Ch. 99. Members of the public can attend in-person to provide comment. Check the town website for the published agenda.
Town Council Info
Week 4–5 — May 18–31
25
Mon
May
HolidayCommunity
Memorial Day — Town of Windsor Ceremony
📅 Monday, May 25, 2026 📍 Windsor, CA
Windsor honors its veterans and fallen military heroes each Memorial Day with a community ceremony. Town offices, many businesses, and Sonoma County Transit may operate on holiday schedules. Check the Town website for ceremony details and time as the date approaches.
Town of Windsor Website

Recurring Events Every Week in May

🌿

Windsor Certified Farmers Market

Every Sunday, 9:00 AM–12:30 PM through December. Fresh local produce, artisan goods, flowers, food vendors, and themed special events on Windsor Town Green. 25th Anniversary season in 2026!

Visit Windsor Farmers Market →
🍷

Tasting Notes Wine Lounge

Windsor’s downtown wine bar hosts regular tastings, live music nights, and community events. Check their calendar for May happenings — comedy nights and live performances are a regular feature.

Tasting Notes Windsor →
🎨

Multimedia Art Fridays

Every Friday, 9:30 AM–12:30 PM at Windsor Senior Recreation Center. Open to ages 50+ — residents and non-residents welcome. Fee: $8. A creative weekly gathering for visual arts exploration.

Town Calendar →
⛪

Windsor Community Churches

Windsor’s faith community is active with weekly services, special May programming, and community outreach. Check individual church websites for Mother’s Day and Memorial Day services.

Windsor Chamber Directory →
🎓

Windsor Unified School District

May brings end-of-year concerts, spring athletic events, graduation ceremonies, and community school events across Windsor’s schools. Check WUSD’s calendar for school-specific events.

Windsor Unified School District →
🏛️

Town Council — 1st & 3rd Wednesdays

Regular Town Council meetings are held the 1st and 3rd Wednesday of every month at 6:00 PM in the Civic Center Council Chambers. Open to the public; agendas posted in advance.

Agendas & Meetings →

🍇 Windsor Wineries Open in May

Spring is prime tasting season in Sonoma County wine country. These Windsor-area wineries offer tasting room experiences, special events, and vineyard tours throughout May.

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