Lucky you. You just found LEXtoday’s Plan Ahead, a list of some of the biggest events to plan for that are taking place throughout the Horse Capital of the World each month.
Take out your calendar, grab your day planner, or text all your friends — these are the top events we recommend heading to this month. Psst: Don’t forget to bookmark this page and come back; we update our guide monthly.
(Don’t see anything you like? Check out our full events calendar.)
Seasonal
Christmas Vendor Market | Saturday, Nov. 22 | 10 a.m.-4 p.m. | Local Roots KY, Winchester | Shop local for handmade goods, home decor, and seasonal treats.
Turkey Eve Bash + Friendsgiving | Wednesday, Nov. 26 | 6-11 p.m. | The Obstinate Sons | Kick off the holiday weekend with drinks, friends, and live music.
Thanksgiving Brunch Buffet by Infinity: Rooftop Restaurant + Bar | Thursday, Nov. 27 | 11 a.m. | Marriott City Center | $64 | Enjoy panoramic city views with a chef-crafted Thanksgiving buffet.
The Kentucky Shop Black Friday Sip and Shop Sale | Friday, Nov. 28-Saturday, Nov. 29 | Times vary | Manchester Music Hall | Sip local drinks and snag Kentucky-made gifts during this two-day sale.
Feral Folk Winter Market | Sunday, Nov. 30 | 11 a.m.-4 p.m. | Greyline Station | Browse 50+ makers, vintage vendors, and local food booths at this indie winter market.
For the fam
The Legend of Sleepy Hollow | Saturday, Nov. 1-Saturday, Nov. 8 | Times vary | Lexington Children’s Theater | $17+ | Washington Irving’s classic tale gets a kid-friendly twist in this family stage performance.
Wake Up Santa! | Wednesday, Nov. 5 | 5:30 p.m. | Fayette Mall | Free | Help welcome Santa to town as he officially kicks off the holiday season with music and cheer.
Blippi: Join The Band Tour! | Sunday, Nov. 9 | Times vary | Lexington Opera House | $50+ | The energetic YouTube star brings music, learning, and fun to life for kids of all ages.
Santa Train | Saturday, Nov. 29 | Times vary | Bluegrass Railroad Museum, Versailles | $20+ | Ride the rails with Santa and Mrs. Claus through the Kentucky countryside.
Music + comedy
Open Mic Night | Tuesday, Nov. 4 | 7 p.m. | Comedy Off Broadway | $6 | Catch Lexington’s local comics test out new material — or take the stage yourself.
A Day To Remember & Yellowcard - Maximum Fun Tour | Thursday, Nov. 6 | 6:15 p.m. | RUPP Arena | $26+ | Rock out to pop-punk favorites A Day to Remember and Yellowcard on their co-headlining tour.
Rumours ATL: A Fleetwood Mac Tribute | Thursday, Nov. 13 | 7 p.m. | Manchester Music Hall | An orchestral, high-energy tribute to Fleetwood Mac’s greatest hits.
Get social
Winter Art Market | Saturday, Nov. 1 | 11 a.m.-6 p.m. | Midway Art Studios, Midway | Shop handmade gifts, jewelry, ceramics, and fine art while supporting local artists.
Poetry at the Table | Wednesday, Nov. 5 | 5:30 p.m. | Kenwick Table | Free | Join featured poets and an open mic lineup for an evening of creativity and community.
Fashion and Mrs. Lincoln | Sunday, Nov. 9 | 2-4 p.m. | Mary Todd Lincoln House | $10+ | Explore 19th-century fashion and Mary Lincoln’s personal style through stories and exhibits.
Garden Exotica Cookbook Release and Photography Exhibition | Monday, Nov. 10 | 7 p.m. | Joseph-Beth Booksellers | Free | Celebrate the release of Garden Exotica with a book signing and photo showcase.
Burgoo and Trivia at the Springs | Saturday, Nov. 15 | 6-8 p.m. | McConnell Springs | Free+ | Warm up with burgoo, join in trivia, and enjoy a cozy evening in nature.
Classes
Cannoli Making Class | Sunday, Nov. 2 | 1-2:30 p.m. | Harkness Edwards Vineyards, Winchester | $48 | Learn to roll, fill, and decorate fresh cannoli while enjoying vineyard views and wine pairings.
Snowflake Pastry Braid Making Class | Saturday, Nov. 15 | 12-1:30 p.m. | Harkness Edwards Vineyards, Winchester | $58 | Create your own festive pastry braid and enjoy a glass of wine as you bake.
Holiday Doormat Painting Class | Saturday, Nov. 15 | 2:30-4 p.m. | Harkness Edwards Vineyards, Winchester | $58 | Customize a winter-themed doormat while sipping wine and getting crafty.
Mosaic Art Class: Turkish Lamp Workshop | Saturday, Nov. 22 | Times vary | Hyatt Place | $113+ | Craft your own colorful glass mosaic lamp with guidance from instructors.
Have an event of your own you want to share with us? Follow these easy steps to add your events to our calendar:
- Go to our Events page.
- Click “Add Event” in the top right-hand corner.
- Make sure to include a link and fill out important information like the date, time, location, and price of your event.
- Click “Submit,” and you’ve just added an event to our website calendar.