Small Town Halloween: Trick-or-Treating & Town Square Gathering

There’s something truly special about fall in Augusta. As the leaves begin to turn and the air gets crisp, our charming little town transforms into a postcard-worthy autumn retreat. October and November are packed with cozy celebrations, community traditions, and winery events — and I’d love nothing more than to host you right here at The H.S. Clay House while you’re soaking it all in.

I always say Halloween in Augusta is what you wish Halloween still felt like — fun, neighborly, and full of charm (with just a little spooky on the side!). Every year, the town comes alive with costumed kids going door to door, and then everyone gathers in the square for a casual fall celebration with chili, soup, and friendly faces.

If you’re curious or want to join in the fun, I’d be delighted to tell you more about it — just ask! It’s one of my favorite things we do as a community, and I love sharing it with guests.

🍎 While you’re here, don’t miss the chance to go apple and pumpkin picking at Centennial Farms — it’s the perfect fall outing, especially if you want to bring a little piece of Augusta home with you.

🍷 Wicked Wine Hop – October 25

One of the most fun events of the season! The Wicked Wine Hop is back in Augusta and takes place on Saturday, October 25th. Grab your friends, put on your favorite costume (or come as you are), and spend the day hopping between four local wineries for wine, music, and spooky good vibes.

Here’s what’s included with your $15 ticket:

• 🎭 Costume contests at every winery – enter more than one!
• 🎶 Live music at all four locations
• 🛍️ Vendors + Cellar Tours (Mt. Pleasant)
• 🍷 Tasting voucher + Pumpkin Passport
• 🎁 Winery swag & goodies in your check-in bag
• 🎉 Chance to win prizes when you collect all pumpkin pieces!

🕚 Check-in starts at 11AM at Augusta Winery.
🎟️ Get your tickets here »

If your interested in joining, let me know and I will help get you set up! 

🍂 Big Weekend of Winery Events – November 15

Mark your calendar: the weekend of November 15th is packed with local winery experiences across Augusta and beyond.

Participating wineries include:

• Montelle Winery
• Augusta Winery
• Balducci Vineyards
• Mount Pleasant Estates

Here’s a peek at what’s happening:

🎶 Live Music with Ed Belling
🕐 1–4PM at Augusta Wine & Beer Garden
A soulful mix of acoustic and contemporary tunes — perfect with a glass of wine and vineyard views.

🎨 Holiday Cork Craft & Sip at Balducci
🕑 2–5PM | $25 Ticket
Create a festive holiday cork craft, enjoy a drink, and cozy up with music and firelight. Ugly Christmas sweaters encouraged!
Reserve your spot: Click here »

🍫 Wine with Friends – Port Edition at Noboleis
🕛 12–5PM | FREE Entry
Featuring their favorite small batch ports and local vendors like:

• Wanderlust Chocolate
• Bootleggers Cigars & Apothecary
• Wilrose Charcuterie
• Fallen Brothers Spirits

No ticket needed — just come sip and shop!  Come stay with me and enjoy the festivities! 

🎁 Cozy Winter Stays & Gift Certificates

As we roll into the holidays, don’t forget: a stay at The H.S. Clay House makes the perfect gift. Whether you’re looking for a romantic winter getaway or a thoughtful present for someone special, I offer gift certificates and off-season winter rates that make it easy to treat the ones you love.

Come relax, sip wine, and experience all the seasonal magic Missouri Wine Country has to offer. I’d love to host you.

Plan Your Fall Getaway Today

Augusta is full of reasons to visit this fall—and I’d love to host you at The H.S. Clay House Bed & Breakfast.

Rooms are filling quickly for key weekends, so don’t wait too long! Let’s make this your most magical fall yet.

🍂 Book your next stay now – I can’t wait to welcome you.

– Kelly