Holiday Hop
Nov
7
to Nov 10

Holiday Hop

Visit beautiful downtown Winchester's many great shops and restaurants to kick off your holiday shopping with refreshments, raffles, give-aways and specials at participating locations!

Thursday, November 7 open until 7 PM
Friday, November 8 open until 6 PM
Saturday, November 9 open until 5 PM
Sunday, November 10 open from 1-4 PM* 

*Select shops open on Sunday 

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Small Business Saturday
Nov
30
10:00 AM10:00

Small Business Saturday

Shop downtown Winchester on the Saturday after Thanksgiving for "Black Friday" deals without the crowds and hustle. Downtown Winchester offers unparalleled personal, friendly service & we have everything you need for everyone on your list this holiday season.

Check back for more info!

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Oct
5
10:00 AM10:00

Kentucky Hemp Harvest Fest

An exciting day filled with street vendors, educational presentations, demonstrations, farm tours, music, food and family fun.

The street fair will begin at 10:00 am and will last until 6:00 pm. on Main St. North of Broadway for the festival. Presentations and discussion panels will be held in the historic Leeds Theater, with screenings of the USDA film “Hemp for Victory” between events. A shuttle will run from the festival site to the Bluegrass Heritage Museum for tours of their newly revised hemp exhibit and hemp processing demonstration.

For more information click here!

For information about Kentucky Hemp Harvest Fest Dinner at the Bluegrass Heritage Museum on October 4 click here!

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Rock the Block with Remember When Cruiserz: One Way Street
Sep
13
7:00 PM19:00

Rock the Block with Remember When Cruiserz: One Way Street

This event was originally scheduled for 6/7.

One Way Street has a wide repertoire ranging from Journey to country hits. One Way Street is presented by Traditional Bank.  Traditional Bank is proud of its community banking heritage, and proud to continue the tradition of providing exceptional service to the people and businesses in the cities and towns they call home

Free kids activities (bouncy house!) are presented by Community Trust Bank , which is committed to providing customers with the highest standards of personalized customer service. 

Remember When Cruiserz will be hosting a classic car cruise-in on N. Main as part of this fun filled night!

Food and drink:
West Sixth Brewing Beer Garden
Harkness Edwards Vineyards
Local Eateries
Bella Shaved Ice
D & D Concessions
Bluegrass Kettle Masters

Rock the Block is brought to you by the generous sponsorship of Traditional Bank. Traditional Bank is proud of its community banking heritage, and proud to continue the tradition of providing exceptional service to the people and businesses in the cities and towns they call home

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Rock the Block with Remember When Cruiserz: Boogie G & the Titanics
Aug
23
7:00 PM19:00

Rock the Block with Remember When Cruiserz: Boogie G & the Titanics

Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street! 

Boogie G and the Titanics is the region's number one party band - and they proved it on the streets of downtown Winchester in 2016 when they brought the crowd to their feet playing R&B, Soul, Funk, Class Rock hits.

Boogie G is proudly presented by Kentucky Bank.  Kentucky Bank is a community bank at heart that delivers Premier Customer Service and financial performance. Understanding its communities and their needs is important to Kentucky Bank.  They have been a part of Kentuckians’ financial solutions since 1851.

Winchester’s very own Dancer’s Pointe will perform during intermission!

Free kids activities (bouncy house!) are presented by Community Trust Bank , which is committed to providing customers with the highest standards of personalized customer service. 

Remember When Cruiserz will be hosting a classic car cruise-in on N. Main as part of this fun filled night!

Food and drink:
West Sixth Brewing Beer Garden
Harkness Edwards Vineyards
Local Eateries

More info coming soon!

This may be the last official Rock the Block, but you won’t want to miss the Daniel Boone Pioneer Festival Street Dance on August 30! Same great location!

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Sip & Stroll
Aug
23
5:00 PM17:00

Sip & Stroll

Join us for Downtown Winchester's annual wine tasting event on August 23 during Rock the Block.  The event features our beautiful downtown shops, vendors and regional wineries. Sip, shop and stroll! 

Check back for more info!
 

 

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Rock the Block with Remember When Cruiserz: Bent Penny
Jul
19
7:00 PM19:00

Rock the Block with Remember When Cruiserz: Bent Penny

Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street! Bent Penny is central Kentucky’s premiere rock band and 2017 winner of the Lexington Music Award’s Best Rock Band Award! Bent Penny is presented by Central Bank.

Enjoy a sneak peek of Leeds Center for the Arts’ production of Mamma Mia! The cast will perform during intermission.

Central Bank has been serving the people and communities of the Commonwealth since 1946. Its bankers are actively involved in all aspects of community life.

Free kids activities (bouncy house!) are presented by Community Trust Bank , which is committed to providing customers with the highest standards of personalized customer service. 

Remember When Cruiserz will be hosting a classic car cruise-in on N. Main as part of this fun filled night!

Food and drink:
West Sixth Brewing Beer Garden
Harkness Edwards Vineyards
Local Eateries

More info coming soon!

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Rock the Block with Remember When Cruiserz: Ray's Music Exchange
May
17
7:00 PM19:00

Rock the Block with Remember When Cruiserz: Ray's Music Exchange

Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street presented by WCC Chamber of Commerce, Tourism and Main Street Winchester.

Free kids activities (bouncy house!) are presented by Community Trust Bank.

Ray’s Music Exchange plays all your favorites from Boz Skaggs to Tom Petty.

Remember When Cruiserz will be hosting a classic car cruise-in on N. Main as part of this fun filled night!

Food and drink:
West Sixth Brewing Beer Garden
D&D Concessions
Local Eateries

More info coming soon!

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Winter Walk About
Feb
7
5:00 PM17:00

Winter Walk About

Winchester's Downtown Businesses present the 3rd annual Winter Walk About on Thursday, February 7 from 5:00-8:00 PM. The open house features extended hours, prizes, sales, special guests and more. It's the perfect time to pick up something for your Valentine.

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Christmas Parade presented by Masons of Right Angle Lodge
Dec
2
5:00 PM17:00

Christmas Parade presented by Masons of Right Angle Lodge

DUE TO INCLEMENT WEATHER THE PARADE HAS BEEN RESCHEDULED FOR SUNDAY, DECEMBER 2 AT 5 PM.

PLEASE SEE RULES FOR PARTICIPATION BELOW FOR UPDATED TIMES

It's a Winchester tradition! Celebrate the holidays at our annual Christmas Parade

Thank you to our sponsors the Masons of Right Angle Lodge and Bypass Rental!

Parade theme: Santa’s Workshop
Registration fee: $10

Rules for Participation

Float Contest Info (Optional)
First Place $500
Second Place $100
Third $50

PARADE REGISTRATION ENDS NOVEMBER 21

The 2018 Christmas Parade in downtown Winchester is brought to you by Masonic Lodge 233.

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Small Business Saturday
Nov
24
10:00 AM10:00

Small Business Saturday

Shop downtown Winchester on the Saturday after Thanksgiving for "Black Friday" deals without the crowds and hustle. Downtown Winchester offers unparalleled personal, friendly service & we have everything you need for everyone on your list this holiday season.

Before you start your shopping adventure, stop by our Neighborhood Welcome Station for a free Shop Small tote filled with #shopsmall swag and goodies from our downtown businesses. We'll be there with our partner Bluegrass Small Business Development Center from 10AM until we run out (or 2 PM if that happens first)!

Click here for a map of our shops and restaurants!

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Holiday Hop
Nov
8
to Nov 11

Holiday Hop

Visit beautiful downtown Winchester's many great shops and restaurants to kick off your holiday shopping with refreshments, raffles, give-aways and specials at participating locations!

Thursday, November 8 open until 7 PM
Friday, November 9 open until 6 PM
Saturday, November 10 open until 5 PM
Sunday, November 11 open from 1-4 PM* 

*Select shops open on Sunday 

Click here for a map of participating businesses

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Halloween MAINia
Oct
30
6:00 PM18:00

Halloween MAINia

***RESCHEDULED: HALLOWEEN MAINIA WILL TAKE PLACE ON TUESDAY, OCTOBER 30 FROM 6 - 8 PM DUE TO WEATHER***

Trick or Treat on Main Street! All are welcome to this Free and Family Friendly event.

Main Street will be closed to traffic from Lexington Avenue to Washington Street for a spooktacularly safe evening. 

Candy and other treats provided by our wonderful downtown & community businesses, organizations and partners. 

For more information about handing out treats, click here.

To sign up to hand out treats, click here.

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Rock the Block: The Classics
Aug
23
7:00 PM19:00

Rock the Block: The Classics

RESCHEDULED (from August 17)! Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street! 

Local legends The Classics  are a down home, make ya wanna shake your bum bum, rowdy dowdy, band that plays the classics you know and love. 

Rock the Block: The Classics is proudly presented by Kentucky Bank.  Kentucky Bank is a community bank at heart that delivers Premier Customer Service and financial performance. Understanding its communities and their needs is important to Kentucky Bank.  They have been a part of Kentuckians’ financial solutions since 1851.

More info coming soon!

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Sip & Stroll
Aug
23
5:00 PM17:00

Sip & Stroll

Join us for Downtown Winchester's annual wine tasting event on August 23.  The event features our beautiful downtown shops, vendors and regional wineries. Sip, shop and stroll! 

22 shops. 25 vendors.  6 wineries. 

Chenault Vineyards
Hamon Haven Winery
Harkness Edwards Vineyards
Jean Farris Winery
McIntyre's Winery
Rose Hill Farm Winery

Click here for an interactive event map, participating businesses and full list of vendors.
 

 

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Rock the Block: Kimberly Carter & Carryin' On
Jul
28
7:00 PM19:00

Rock the Block: Kimberly Carter & Carryin' On

Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street!

Local favorites Kimberly Carter & Carryin' On is fronted by Judge Kimberly Walson under her maiden name. This band of local musicians has played from Nashville to Louisville to Pikeville.  They have their own genre: Rock-infused Country & Blues and are the house band at Clark County's own Waterfront Grille & Gathering.

Rock the Block: Kimberly Carter & Carryin' On is proudly presented by Central Bank. Central Bank has been serving the people and communities of the Commonwealth since 1946. Its bankers are actively involved in all aspects of community life. 

*This event was originally scheduled for 7/20, but was postponed due to inclement weather.

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Rock the Block: Encore of Lexington
Jun
8
7:00 PM19:00

Rock the Block: Encore of Lexington

 Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street!

Encore of Lexington is back! Performing such Artist as: Sam Cook, Joss Stone, Bruno Mars, Maxwell, Patrice Rushing, Robin Thick, Marvin Gay, Aretha Franklin, DNCE, Michael Jackson, Doobie Brothers, Steely Dan, Chaka Khan and many, many more!

Rock the Block: Encore of Lexington is brought to you by the generous sponsorship of Traditional Bank. Traditional Bank is proud of its community banking heritage, and proud to continue the tradition of providing exceptional service to the people and businesses in the cities and towns they call home

And our June date kicks of the ONE AND ONLY BEER CHEESE FESTIVAL IN THE WORLD!

More info coming soon!

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Rock the Block: The Fever
May
18
7:00 PM19:00

Rock the Block: The Fever

Our summer concert series is back by popular demand! Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street presented by the WCC Chamber of Commerce, Tourism and Main Street Winchester.

Featuring The Fever. The Fever is a band that can get the party started and have everyone dancing the night away!

Fun: We'll have GIANT Jenga, sidewalk chalk, a bouncy house and more!

Food: Party Tent USA's food truck will feature rotisserie chicken, hamburgers/cheeseburgers, hot dogs, sausages, popcorn, funnel cakes, and snow cones

Bonus: Visit the West Sixth Brewing beer tent!

Thank you to ByPass Rental & Hardware for providing porta-potties!

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Downtown Shop Hop
Mar
24
10:00 AM10:00

Downtown Shop Hop

Hop into the shops this spring! Downtown Winchester welcomes you to explore the district during the Downtown Shop Hop Each merchant will be offering unique promotions and exclusives, making it the perfect time to get a head start on sprucing up your garden, shopping for graduation, Mother's Day, wedding showers, or updating your spring wardrobe!  Click here for a map of participating shops.

Tune in here for updates on contests, prizes, promotions and more!

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Winter Walk About
Feb
8
5:00 PM17:00

Winter Walk About

Winchester's Downtown Business Group presents the 2nd annual Walk About Winter on Thursday, February 8 from 5:00-8:00 PM. The open house features extended hours, prizes, sales, special guests and more. It's the perfect time to pick up something for your Valentine.

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2017 Christmas Parade presented by Masons of Right Angle Lodge 233 F&AM
Dec
2
6:00 PM18:00

2017 Christmas Parade presented by Masons of Right Angle Lodge 233 F&AM

Celebrate the holidays in downtown Winchester with our annual Christmas parade!

This year’s theme, A Magical, Musical Christmas, celebrates the sounds, memories and traditions we all hold dear each holiday season and invites participants and attendees to think about all the special songs and magical moments that mean Christmas to us. 

To help us celebrate a Magical, Musical Christmas, we are honored to have Martin Family Circus serve as our grand marshal this year! Led by Grammy-winning Winchester native, Paul Martin, "this self-contained vocal-driven melodic band of 2 parents and 4 kids packs a punch with their rich stack of family harmonies in a soaring blend, which Rolling Stone magazine calls 'exuberant.'" 

Whether it’s a favorite memory, movie, experience, emotion or tradition, parade registrants are asked to capture what a Magical, Musical Christmas means to them with their entry.

Rules for Participation

(Optional) Float Judging Information
First Place $500
Second Place $100
Third $50

The 2017 Christmas Parade in downtown Winchester is brought to you by Masonic Lodge 233.

PARADE REGISTRATION ENDS NOVEMBER 20, 2017

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Holiday Hop
Nov
9
to Nov 11

Holiday Hop

Visit beautiful downtown Winchester's many great shops and restaurants to kick off your holiday shopping with refreshments, raffles, give-aways and specials at participating locations!

Thursday, November 9 open until 7 PM
Friday, November 10 open until 6 PM
Saturday, November 11 open until 5 PM

Select shops open on Sunday from 1- 4 PM, too!

Click here for a map of participating businesses.


 

View Event →
Halloween MAINia
Oct
31
6:00 PM18:00

Halloween MAINia

Trick or Treat down Main Street! All are welcome to this Free and Family Friendly event. Main Street will be closed to traffic from Lexington Avenue to Washington Street for a spooktacularly safe evening. 

Candy and other treats provided by our wonderful downtown & community businesses, organizations and partners. If your business or organization would like to hand out treats, sign up here.

For more information about handing out treats, click here.

View Event →
Urban Loft Tour
Sep
24
2:00 PM14:00

Urban Loft Tour

Eclectic, diverse and full of heart. Welcome to downtown Winchester!

Downtown Winchester offers the best of small town urban living: historic buildings, modern amenities, public art, walkable neighborhoods and, best of all, affordability!
Come and explore the iconic architecture and hidden gems tucked into the downtown district. You will be inspired by what you find!

This is a rare opportunity to explore the interiors of some of the residential and commercial properties that make downtown Winchester unique.

The Urban Loft Tour has something for everyone, from young professionals to empty-nesters, as well as those interested in historic preservation, interior design, and most importantly:  small town urban living!
 

Thank you to our sponsors Block + Lot and Winchester Federal Bank!

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Rock the Block: The Classics
Aug
25
7:00 PM19:00

Rock the Block: The Classics

Rock the Block will close out its season with the ever popular The Classics!  The Classics are the best Rock n Roll groups in all of Kentucky. The distinct vocal harmonies and the unmatched musicianship make the Classics a must see band! 

Rock the Block: The Classics is brought to you by WCC Chamber of Commerce, WCC Tourism and Main Street Winchester

Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street! We'll have GIANT Jenga, sidewalk chalk and more!

Food: Cool down with Bella Shave Ice, grab a slice from Apollo Pizza's food truck or pick up dinner at Heart to Home's Hot Dog StandIn & Out BBQ or Broadway Cafe!

BONUS: If you can't get enough of live music on Main Street, join us in September for the Daniel Boone Pioneer Festival Street Dance brought to you by Winchester Clark County Tourism!

Thank you to ByPass Rental & Hardware for providing porta-potties!

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Sip & Stroll
Aug
10
5:00 PM17:00

Sip & Stroll

New date!!! Join us for our annual summer wine tasting event, Sip & Stroll, featuring Kentucky wineries hosted by our incredible downtown merchants.

Sip. Stroll. Shop!

Click here for a map of participating downtown businesses!

Visiting Vendors and Wineries:

***This event is free and open to all ages. However, wine tasting is restricted to the 21+ crowd, and there is a small charge for each tasting ***

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Rock the Block: Prime Cut presented by Kentucky Bank
Jul
28
7:00 PM19:00

Rock the Block: Prime Cut presented by Kentucky Bank

Rock the Block, our summer concert series, is back by popular demand! Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street!  

Food: Grab a slice from the Apollo Pizza food truck,  In & Out BBQ or Broadway Cafe!

Local legends Prime Cut combines a solid horn and rhythm section with divine vocal harmonies to perform cover tunes by Chicago, Tower of Power, Blood Sweat & Tears and other name acts with a horn base. 

Rock the Block: Prime Cut is proudly presented by Kentucky Bank.  Kentucky Bank is a community bank at heart that delivers Premier Customer Service and financial performance. Understanding its communities and their needs is important to Kentucky Bank.  They have been a part of Kentuckians’ financial solutions since 1851.

Thank you to ByPass Rental & Hardware for providing porta-potties!

 

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Rock the Block:  Boogie G & The Titanics presented by Traditional Bank
Jun
30
7:00 PM19:00

Rock the Block: Boogie G & The Titanics presented by Traditional Bank

Rock the Block, our summer concert series, is back by popular demand! Bring your lawn chairs, blankets and picnics for a great night of music and fun on Main Street!  

Boogie G and the Titanics is the region's number one party band - and they proved it on the streets of downtown Winchester in 2016 when they brought the crowd to their feet playing R&B, Soul, Funk, Class Rock hits.

Rock the Block: Boogie G & the Titanics is brought to you by the generous sponsorship of Traditional Bank. Traditional Bank is proud of its community banking heritage, and proud to continue the tradition of providing exceptional service to the people and businesses in the cities and towns they call home

Thank you to ByPass Rental & Hardware for providing porta-potties!

View Event →