🌿 May in Augusta: Kick Off Your Stay In Wine Country in Style
May is when everything comes to life in Augusta.
The vineyards are green, patios are open, live music fills the air, and nearly every weekend brings something new to experience. If you’ve been thinking about planning a getaway to Missouri Wine Country, this is one of the best times of the year to do it.
From festivals and wine events to relaxing afternoons with live music, May is all about getting out, exploring, and enjoying everything Augusta has to offer.
🗓️ Memorable May Stay Weekends in Augusta
🍷 May 1–3: Art, Wine & Spring Vibes
The first weekend of May blends the final energy of Plein Air with great live music and unique wine experiences.
Highlights:
- 🎨 Golden Ticket VIP Preview Art Sale
- 🎶 Live Music – Arvell & Keithly at Montelle Winery
- 🍽️ Wine with Friends: Farm-to-Table at Noboleis Vineyards
💡 And don’t forget — Cinco De Mayo is right around the corner (May 5th), making this a fun long weekend to sneak away for a quick trip.
💐 May 8–10: Mother’s Day Weekend in Wine Country
This is one of the most meaningful weekends to plan a stay.
Whether you’re celebrating Mom, planning a girls’ weekend, or just looking for a relaxing getaway, Augusta offers the perfect setting.
Highlights:
- 🍝 Pasta Friday at Balducci Vineyards
- 🎶 Live Music – The Friendly Degenerates at Montelle Winery
- 🥂 Mother’s Day Brunch
💐 We’ll also be doing something special here at The Clay House for Mother’s Day — more details coming soon!
👉 Looking for a thoughtful gift?
A getaway to Wine Country makes an unforgettable Mother’s Day surprise, and our Gift Certificates are a perfect way to make that happen.
Even better — they can be used later this summer when things really heat up, including during the Augusta Summer Concert Series, one of the most popular times to visit.
🍇 May 15–17: Missouri Wine Festival Weekend
This is a big one.
The Missouri Wine Festival brings together wineries, live music, and wine lovers for one of the most exciting weekends of the season.
👉 Lastest News About The Missouri Wine Festival
Across Augusta and nearby wineries, you’ll find:
- 🍷 Tastings and special releases
- 🎶 Live music throughout the weekend
- 🍇 Events at Montelle, Balducci, Noboleis, and Defiance Ridge
Additional highlights:
- 🎶 Live Music – Ribtips Rogers at Montelle
- 🎸 Augusta Ramble – Acoustic 420 Tribute
💡 Planning a group trip?
This is a perfect weekend to rent the entire H.S. Clay House and make it your home base. When you do, Kelly can help coordinate special touches like wine tastings, themed gatherings, or group-friendly experiences to make your stay even more memorable.
🇺🇸 May 22–24: Memorial Day Weekend Getaway
Kick off summer early with a relaxing and festive Memorial Day weekend in Augusta.
Highlights:
- 🎶 Live Music – Janet Martin & Greg Worzel at Montelle
- 🍷 Sip & Salute Memorial Day Event
- 🚤 Memorial Day BBQ Cruise on the Miss Augusta
This is one of the most fun weekends to gather friends, relax, and enjoy the start of summer.
🎶 May 29–31: Spirits, Music & Distillery Fun
Close out the month with another packed weekend of entertainment. If you enjoy spirits, get excited about the Missouri Spirit Fest!
Highlights:
- 🎶 Live Music – The Bedlam Brothers at Montelle
- 🥃 Missouri Spirit Festival
- 🍸 Music & Spirits Events at Stone Ledge Distillery
Between wineries and distilleries, this is a great weekend for those who love exploring local flavors.
🎨 Still Time to Plan A Plein Air Stay
The Augusta Plein Air Art Festival carries right into the start of May, wrapping up one of the most exciting times of the year for art lovers.
From paint outs and gallery previews to exclusive events like the Golden Ticket VIP Art Sale, this is your last chance to experience the festival before it closes.
👉 Read Our Full Plein Air Guide
🎷 Looking Ahead to June
The momentum keeps building into June with even more great events:
If you’re thinking about a summer visit, now is the time to start planning.
🏡 Why Stay in an Augusta Bed & Breakfast Over Airbnb?
If you’re planning a trip to Augusta, where you stay can make all the difference.
At a Bed & Breakfast like The Clay House, you’re not just booking a place to sleep — you’re stepping into a curated experience. From fresh breakfasts and local recommendations to personalized touches and hosted experiences, it’s a completely different kind of stay.
🌸 Plan Your May Stay In Augusta Now!
May is one of the best times to visit Augusta — full of energy, events, and opportunities to relax and reconnect.
Whether you’re planning a Mother’s Day surprise, a girls’ weekend, or a group getaway, there’s something happening every weekend to build your trip around.
And if you’re looking to make it even more special, consider renting the entire H.S. Clay House and turning your visit into a fully customized experience.
We’d love to have you join us.
Take a look at availability and start planning your May stay — we hope to see you soon.
