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The inaugural Annual Bluegrass Rallye Raid will take place from June 3 to June 6, 2026, in Lewisburg, Pennsylvania. Organized in partnership with Backroads of Appalachia and Zacker Adventures, the event features four days of navigation challenges for rally, adventure bikes, side-by-sides, and trucks. Participants will use a digital roadbook via the Terra Pirata app […] |
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Gearheads will gather for the First Friday Cruise-In in Downtown Paintsville. The event takes place in the City Parking Lot on the first Friday of each month. Participants can expect to see classics, hot rods, trucks, and more. The event is open to everyone and provides an opportunity to cruise in and hang out. |
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Gravity Falls Motorsports hosts a monthly Cars & Coffee event on the first Saturday of each month from May through October. The gatherings take place from 9 a.m. to 11 a.m. at 329 E. Main St. in Morehead. Eagle GMC sponsors the series. 
Downtown Jenkins KY Cruise In & Burnouts, first Saturday May-October, 4pm in the park. Family friendly with door prizes and food. Old Hotrods. Win an $10 2026 Truck Raffle; tickets $10 each or 6 for $50. Winner will be drawn at the October 2026 Jenkins Cruise In. Must be 18 or older and be reachable […] 
The 2026 Monthly Main Street Cruise In's will take place on the first Saturday of each month from April through September. The events will start at 5:00 PM and will be held in the Town Square of Beattyville, KY.
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Charlie's Grove Cruise-In is scheduled for June 6, 2026, from 5:00 PM to 9:00 PM at 2700 Muses Mill Rd. The event will feature hot food, a silent auction, and inflatables. |
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Shades Of Days Before Car Club will host the Motors In The Holler Car Show on June 7, 2026. The event will take place at Battle Of Leatherwood Battlefield from 1:00 PM to 6:00 PM. Awards will be given for Top 50, Best GM, Best Ford, Best Mopar, Best Import, Best AMC, Best Rat Rod, […] |
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The Shopville Community Cruise In occurs on the 2nd Friday of each month from April through October. The event begins at 5:00 PM and takes place at Shopville Park. 
Join us for a fun evening of classic cars, cool trucks, hot rods, and great company! Bring your ride or just come out and walk around, check out the vehicles, and enjoy the atmosphere. This is a relaxed, family-friendly event where car lovers can connect, show off their builds, and appreciate everything from vintage classics […] |
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The Morning Cruise offers free coffee and donuts on the second Saturday of each month. The event takes place at the Danville Church Of God Parking Lot.
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The Kentucky State Police Post 9 Outdoor Car Show will take place on June 13th, 2026, for the KSP Post 9 in Pikeville, KY. The location is Cassidy Blvd behind Applebee's. Registration will be from 9:00 AM to 1:00 PM, with a registration fee of $20. Awards will be presented after judging is completed. All […] 
The Cumberland Valley Cruise-In will take place in Corbin, Kentucky. Events are scheduled for May 9, June 13, July 11, and October 10 in 2026.
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HC Cheer is hosting a Car and Motorcycle Show on June 13, 2026 at the Harlan Mall parking lot. Show hours are 10AM - 3PM. Registration is $15. Categories shown include Best GM, Best Ford, Best Mopar, Best of Show, and Best Motorcycle.
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The Relay For Life Charity Car Show will take place on June 13, 2026, at The Drive-In Diner. The event supports the American Cancer Society. The car show is scheduled to run from 12:00 PM to 3:00 PM. |
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The Gate City Cruise-In is scheduled to start on April 17, 2026, at the Boyd County Judicial Center in Catlettsburg, Kentucky. The event will start at 5:00 PM and continue until dark. It promises classic cars, good food, and good times. 
The Gate City Cruise-In will feature classic cars, food, and entertainment. The event is scheduled for July 5, 2026, starting at 5:00 PM. The location for the event is the Boyd County Judicial Center. |
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The Climax Volunteer Fire Department will hold its 5th annual car show on Saturday, June 20, 2026, from 10:00 AM to 2:00 PM at 7436 Climax Rd, Mt Vernon, KY 40456. Entry fee for vehicles is $15 while spectator admission is free and donations are accepted; judging begins at 12:00 PM. The show will feature […]
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The Hazel Green Food Project hosts its 2nd Annual Car, Tractor, and Motorcycle Show on June 20 from 10 a.m. to 2 p.m. at 1225 Kentucky 205 North in Hazel Green, Kentucky. Registration runs from 10 a.m. to 1 p.m. with a $15 entry fee. Admission is free to the general public.Awards will be presented […] 
This recurring car cruise takes place every third Saturday from 3 p.m. to 7 p.m. on Cumberland Avenue in downtown Middlesboro, rain or shine. The next scheduled dates are June 20, July 18, Aug. 15, Sept. 19, and Oct. 17. Each event features a $50 drawing with 20 winners per show. The drawing takes place […] 
Cruisin' the Crater hosts its Show & Shine on Cumberland Avenue in downtown Middlesboro, Ky., welcoming owners of custom, classic, muscle cars and hot rods to display their vehicles from 3 to 7 p.m. The event takes place rain or shine. Attendees can enjoy live music from Gary's Sound Machine and browse local businesses along […] 
The Gearheads 3rd Saturday Cruise-In takes place on the third Saturday of each month from 4:00 PM until dark. The event features door prizes every 30 minutes. A swap meet will be held at each cruise-in. The location for the event is Citizens National Bank. |
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The 7th Annual Eubank Fathers Day Car Show will be held at Eubank Park on June 21, 2026. The event is scheduled from 12 PM to 4 PM and will feature special guests from the Knights and Dames Car Club. Prizes will be awarded in various categories. Concessions will be available for attendees. The admission […] |
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The Somernites Cruise hosts its 10th annual "Somernites Cruise Truckin' Nationals" showcase on June 27 in Somerset, KY. The event is sponsored by Auto Kustoms & LMC Truck. A "Young Guns" special display and raffle truck drawing will be featured. The showcase is part of the monthly cruise series that runs through October. Additional events […] |
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Gearheads will gather for the First Friday Cruise-In in Downtown Paintsville. The event takes place in the City Parking Lot on the first Friday of each month. Participants can expect to see classics, hot rods, trucks, and more. The event is open to everyone and provides an opportunity to cruise in and hang out. 
East KY Gearheads hosts a Friday night cruise-in at Citizens Bank on Broadway. The event runs from 5 p.m. until dark and features classic cars and socializing. |
4 events,
Gravity Falls Motorsports hosts a monthly Cars & Coffee event on the first Saturday of each month from May through October. The gatherings take place from 9 a.m. to 11 a.m. at 329 E. Main St. in Morehead. Eagle GMC sponsors the series.
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The Salyersville 4th of July Celebration Car Show takes place Saturday, July 4 at Salyersville City Park. Registration begins at 10 a.m. Awards will be presented at 2 p.m. The event features free food and door prizes.
Downtown Jenkins KY Cruise In & Burnouts, first Saturday May-October, 4pm in the park. Family friendly with door prizes and food. Old Hotrods. Win an $10 2026 Truck Raffle; tickets $10 each or 6 for $50. Winner will be drawn at the October 2026 Jenkins Cruise In. Must be 18 or older and be reachable […]
The 2026 Monthly Main Street Cruise In's will take place on the first Saturday of each month from April through September. The events will start at 5:00 PM and will be held in the Town Square of Beattyville, KY. |
2 events,
The Gate City Cruise-In will feature classic cars, food, and entertainment. The event is scheduled for July 5, 2026, starting at 5:00 PM. The location for the event is the Boyd County Judicial Center.
The Gate City Cruise-In is scheduled to start on April 17, 2026, at the Boyd County Judicial Center in Catlettsburg, Kentucky. The event will start at 5:00 PM and continue until dark. It promises classic cars, good food, and good times. |
