Annual Events

Discover Maysville's Top Events

Art & Chocolate Festival


Month: April

It’s time to celebrate at the Old Washington Art and Chocolate Festival. Focusing on local artisans and more importantly—chocolate, it’s a delicious opportunity to taste all that this historic district has to offer.

For more information, contact

2024 Vendor application click here.

Maysville Uncorked Wine and Art Festival


Month: June

Cheers to summer! Sponsored by the Maysville Players, Kentucky’s oldest theatrical company, this festival is all about regional wineries—with some beer and bourbon thrown in for fun. Historic, brick lined Market Street is located in the center of town and the venue for this can’t-miss event.

For more information, contact 606-584-4888 or visit
Independence Day Parade & Event


Month: July

Celebrate the Fourth of July in Maysville with a classic parade, fireworks, food, music and shopping. Located in our Entertainment District, you are sure to find plenty of activities to occupy your holiday weekend.

For more information, contact Main Street Director, Caroline Reece at 606-563-5624 ext. 104 or
M2M Paddlefest


Month: July

Enjoy a guided kayak/canoe trip from Manchester, Ohio to Maysville, Kentucky along the Ohio River. Transportation is available if needed and the party ends at O’Rourke’s Pub in Maysville, Kentucky,  just steps from Limestone Landing.

The M2M Paddlefest is sponsored by O’Rourke’s Pub. For more information, contact


Month: August

Is it Munich or Maysville? Hard to tell when this festival comes to town. With Bavarian polka bands, beer trucks, sauerkraut on bratwurst, wiener dog races and polka dancers on every corner, we invite you to join us in raising a stein to Maysville’s German heritage.

This two-day festival is presented by the Maysville Rotary Club. All proceeds go to funding scholarship grants. For more information, visit
Limestone Cycling Tour


Month: September

The Limestone Cycling Tour is excited to be a part of the Kentucky Century Challenge! Cyclists will enjoy the beautiful rolling hills surrounding Maysville and Mason County on our curvy little-traveled back roads. Four routes are offered including a challenging Century, Metric Century and 40 and 22-mile loops. Routes are fully supported with surprise themes at the SAG stops and staffed by community volunteers. It is some of the best cycling in Northern Kentucky and not to be missed!

For more information, visit the website
Simon Kenton Festival

Frontiersmen on horses

Month: September

A two-day historical adventure in the Old Washington Historic District. The Simon Kenton Festival includes presentations from historical heroes such as Simon Kenton and Daniel Boone, pioneer games, music, museum tours, artisans, and much more. This weekend will be sure to provide you with historical knowledge, a treasured keepsake, and memories that will last a lifetime.

For more information, contact

2024 Vendor & Exhibitor application click here.

Pig Out in Maysville

pig-out-web - Copy

Month: September

Pig Out is located at the Lewis & Clark Pavilion in Downtown Maysville. Enjoy music, entertainment and LOTS of food!

All proceeds from this event go to the Shriner’s Transportation Fund. For questions and more information, contact 606-375-6154.
Downtown Halloween


Month: October

On the Saturday before Halloween, bring your little ghosts and goblins to enjoy trick-or-treating in the streets of Downtown Maysville! Merchants pass out treats while the Mason County Public Library hosts activities for kids of all ages. The VFW sponsors a Trunk or Treat in Lewis and Clark Pavilion and provides a hot dog lunch for all.

Continue Halloween celebrations with the Annual Run for Your Life 1-Mile Walk/Run held the last Saturday of the month. Costumes and walking/running with your dog are encouraged. All proceeds benefit the Humane Society of Buffalo Trace.

For more information, contact Main Street Director, Caroline Reece at 606-563-5624 ext. 104 or
Twilight Christmas Parade and Market


Month: December

Plucked from a Hallmark Christmas movie, enjoy Maysville, Kentucky’s Christmas Market coinciding with the Downtown’s Twilight Christmas Parade. As a variety of floats spread holiday cheer, the Christmas Market will features live music, handmade arts and crafts, baked goods and food vendors. Make plans to meet up with Santa afterwards to double check your status on his nice list!

For more information, contact Main Street Director, Caroline Reece at 606-563-5624 ext. 104 or
Frontier Christmas

Celebrate the holidays in the Old Washington Historic District—a historic 1700s village. Handmade arts and crafts vendors line the streets of Old Washington and local shops and museums are open with holiday activities for all ages.

For more information, contact

2023 Vendor Application here.