
Come see the smoke rollin' in Downtown Eastland

Rip's Ribs Cook-Off:
LOCATION: ON THE DOWNTOWN SQUARE
The Annual Rip's Ribs Cook-off is a great day in downtown Eastland to fire up your grill and make your famous Ribs with special rubs, sauces, spices, and more! Enjoy a variety of vendors, and more food options than you have room in your stomach for.
Each year we give away over $2,500 in cash prizes to the top cookoff teams! Entry Fee $125.00. Cooks can enter the “People’s Choice” categories in Appetizers, Beans, Desserts, and/or Meat (excluding St. Louis-style pork ribs) for $10 per category or $30 for all four. Winners in these additional categories will get the entry pot for that category and a year’s worth of bragging rights.
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Rip's Sip, Eat & Shop

Rip's Wine Festival/Sip, Eat & Shop
LOCATION: LUMBER YARD EVENT CENTER & PAVILION, 313 W. MAIN ST
Back by popular demand is the 5th Annual Rip’s Wine Festival held from 12:00 PM-5:00 PM. The Wine Festival will be held at The Lumber Yard Event Center under the Pavilion just 2 blocks from the downtown square. Help us spread the word by marking that you are “Going” and Share our Facebook Event Page with your friends & family.
Rip’s Wine Festival Tickets:
- -Pre-Sale Tickets: $20 for 10 tastings & a souvenir glass
- -At the Door Tickets: $25 for 10 tastings (souvenir glasses are given on a first-come, first-served basis while supplies last)
Pre-sale tickets are available until 5:00 PM on Thursday, April 10th online and can be purchased in person at the Chamber Office located on the first floor of the Connellee Hotel, or from a Chamber Ambassador or Board Member in the weeks leading up to the event. Tickets at the door will be available for purchase at the check-in table during the event. Please note, we are now able to accept card payments at the door but there will be a convenience/processing fee. If you would like to avoid such fees, we suggest purchasing your tickets ahead of time online or bringing cash on the day of.
2025 Winery List:
Food & Shopping Vendors
LOCATION:
RETAIL VENDORS: Lumber Yard Event Center & Pavilion, 313 W. Main St.
FOOD TRUCKS: In front of the Connellee Hotel & Event Center, 209 W. Main St.
The Pink Company - Carnival Food
Ken's Chicken-N-Fish on the Go
DRINK & SNACK VENDORS: On the south side of the Courthouse
PRODUCT & SERVICE INFORMATION BOOTHS: Commerce St. on the downtown square
Jazz Festival & Live Entertainment:
Join us for the Eastland Jazz Festival, presented by the EHS Band, in the heart of downtown Eastland! Enjoy performances from talented high school and junior high jazz bands under the awning behind the Connellee Hotel & Civic Center (209 W. Main St.), right next to the Wine Festival. College jazz bands, along with Eastland and Cisco High School bands, will take the stage at the corner of Olive St. & Lamar St. Plus, catch exciting rock performances on the south steps of the Eastland County Courthouse. Don’t miss this incredible day of live music!
JAZZ BAND SCHEDULE
Behind the Connelle Hotel
Under the Awning
8-8:45 am - Jim Ned 1
9-9:45am - Brock HS
10-10:45am - Wylie HS
11-11:45am - Jim Ned 2
12-12:45pm - Brownwood HS
1-1:45pm- Cooper HS/Clack MS
2-2:45pm - Valley View HS
3-3:45pm - Clyde HS
4-4:45pm - Springtown HS 1/2
5-5:45pm - Dublin HS
Jazz on the Green
Corner of Olive St & Lamar St.
10am - Glen Rose High School
11am - Cisco College
12pm - Hardin Simmons University
1 pm - Eastland High School
2pm - Howard Payne University
3 pm - Cisco High School
4 pm - Gainesville High School
5 pm - Angelo State University
LIVE ROCK
Old Rip Square
South Side of the Courthouse
11:30 - TBA
12:30 - Cognito
1:30 - Brent Elrod
2:30 - Irish Goodbye
