Rotary Golf Tournament – Visit Rolla

Sip N Savor

Aimee — Sat, 02 May 2026 12:00:00 -0500

One of St. James’ favorite traditions is back! 🚗🍇 Sip n Savor takes place May 2 in downtown St. James from Noon–4 PM, and this year’s event celebrates the 100th anniversary of Route 66. Attendees can enjoy delicious sips, tasty bites, and classic Route 66 vibes for a memorable afternoon.

Route 66 Centennial Block Party

Aimee — Sat, 02 May 2026 00:00:00 -0500

Celebrate the Route 66 Centennial with a Block Party in Rolla from 2-7 pm on May 2!

Join us for a fun-filled Route 66 Centennial Kickoff Block Party in downtown Rolla! This FREE event celebrates the legacy of America’s Mother Road with something for everyone.

Enjoy live music throughout the afternoon, explore food trucks and local restaurant specials along Route 66, and keep the kids entertained with family-friendly activities. Every 66 minutes, we’ll be giving away free Route 66 swag (while supplies last), so don’t miss your chance to grab some unique memorabilia.

Beer lovers can raise a glass to the Mother Road with a special Route 66 beer release at Public House Brewing Co. Commemorative cans will be available for purchase, and the beer will be on tap to enjoy!

Whether you’re a longtime Route 66 fan or just looking for a great way to spend a Saturday, this block party is the perfect way to celebrate the 100th anniversary of Route 66. Bring your friends, your family, and your love for this iconic road and make some memories in Rolla!

Schedule of Events

Homestead Market

Aimee — Sun, 03 May 2026 10:00:00 -0500

This years Homestead Market will take place on May 3 from 10 am to 3 pm at 15419 HWY 63 S in Vichy, MO!
$5.00 Admission (12 and under are free)

Every May, The Homestead Market brings together neighbors, makers, and families for a day that feels like stepping into a small-town storybook.
– Wander through rows of handmade goods
– Grab lunch from a food truck
– Tap your toes to live music
– Watch your kids light up in the play area
Come for the treasures, stay for the memories.

Website: https://thehomesteadmarket.square.site/

Event Page: https://www.facebook.com/share/1Az9TLRsto/

Trivia Night

Aimee — Sun, 03 May 2026 14:30:00 -0500

Swafftastic Sunday Funday Alert! Join Prairie Barn Winery for a Sunday trivia event starting at 2:30 PM on May 3. Topic is Sit Coms. Swafftastic BBQ pairs perfectly with wine and trivia fun! It’s the perfect way to spend quality time with the whole family!

For questions, contact Shannon at Shannon@prairiebarnwinery.com or 660-253-0079

Fiesta and Fairways Golf Tournament

Aimee — Mon, 04 May 2026 08:00:00 -0500

Choices for People is hosting a Fiesta and Fairways golf tournament on Monday, May 4th at Oak Meadow Country Club! Save the date – more information to come!

Professional Headshots

Aimee — Wed, 06 May 2026 08:00:00 -0500

Refresh Your First Impression: Free Headshot Event

The Rolla Chamber of Commerce will host a free headshot event on May 6 from 8:00 a.m. to 1:00 p.m. at the chamber office as part of Small Business Week. The event is open to the public and designed to help local professionals update their professional image.

In partnership with Fort Wood Photography, attendees can stop by for a quick, high-quality headshot to use on LinkedIn, company websites, social media, and other professional platforms.

What to Expect:

Professional headshots by Fort Wood Photography
Quick, drop-in format—no appointment needed
One polished image for professional use

Please Note:

One headshot per person
No group photos

Participants are welcome to come and go anytime during the event.

Regional Hiring Event

Aimee — Wed, 06 May 2026 10:00:00 -0500

At the Rolla Regional Spring Hiring Event, you can meet employers face to face, ask questions, and make a real impression.

May 6
10 a.m. to 2 p.m.
National Guard Armory, Rolla

Bring your resume. Come ready to talk. See what opportunities are out there.

You can pre-register and view the full list of employers HERE

Small Business Festival

Aimee — Thu, 07 May 2026 17:00:00 -0500

The Rolla Chamber of Commerce invites the community to the Small Business Festival on May 7 from 5-7 pm at the Downtown Festival Lots, celebrating local businesses and the people behind them!

Sponsored by US Bank, the festival features a variety of vendors, giveaways, door prizes, food trucks, and live community energy—perfect for discovering new favorites and connecting with local businesses.

Free and open to the public. Small business owners interested in participating can contact Programs@rollachamber.org or (573) 364-3577

Youth Racing Clinic

Aimee — Fri, 08 May 2026 00:00:00 -0500

The Rolla Saddle Club will host a youth barrel racing clinic on May 8 & 9 at the Saddle Club grounds. Open to all levels of riding from beginner to advanced.

Friday, May 8 from 6-8 pm

Saturday, May 9 from 8 am to 5 pm

The cost is $35 per student/horse. To reserve your spot please call or text 573-308-7792

Ozark Farms Strawberry Festival

Aimee — Sat, 09 May 2026 10:00:00 -0500

Ozark Farms Strawberry Festival • May 9, 2026 • 10am–3pm
The sweetest day of the year is coming soon – and we’re counting down! We can’t wait to welcome you to the farm for our biggest and best Strawberry Festival yet.

Whether you’re continuing a beloved family tradition or planning your first visit, this day is all about fresh air, sweet strawberries, and memories that last a lifetime.

Here’s what’s in store:
Farm-fresh strawberries
Local shopping vendors
Mini pony rides + face painting
Food trucks
Live music
Bounce houses
Baby chicks + mini goats
Catch-and-release fishing lake

even more fun in the works for 2026!

Admission: FREE
Ozark Farms | 11600 Hwy 72, Rolla MO

Interested in being a Vendor? Click HERE!