Events

September Fourth Fridays Guide

Get ready for an extraordinary evening in historic downtown Ashland! The final Ashland Fourth Fridays of the summer season is upon us, and this year’s celebration is extra special. Join us on September 27, from 5-8 PM, for an event that not only highlights our community’s spirit but also marks a key celebration of Virginia Pride—a spectacular month-long tribute to the LGBTQ community across the state.

A Night of Dynamic Entertainment

The festivities kick off at 5 PM with an impressive lineup of performances by the Ashland Dance Academy at the Ashland Town Hall Pavilion. From the elegance of ballet to the energy of hip-hop and the flair of musical theatre, these talented dancers will bring the stage to life.

Following the dance performances, enjoy a free concert featuring the Ashland Song Contest winner Ginny Ray, who will grace us with her award-winning song. The celebration continues with special performances from other song contest finalists, showcasing their original Center of the Universe-themed creations.

And don’t miss The Sweet Potatoes, a fearless jazz quartet known for their soulful takes on classic covers, innovative originals, and spontaneous jams. With vocal scats, vibrant violin riffs, and a dynamic rhythm section, they’ll have you grooving all night long.


Delicious Bites and Unique Finds

As you enjoy the music and performances, explore an array of vendors around Ashland Town Hall and 110 Thompson Street. TransJam Events, a trans-led service dedicated to organizing fun, inclusive, and engaging local events, will be bringing you a diverse range of vendors offering everything from homemade jams and pastries to original art and tarot readings. 

Treat yourself to sweet and savory crepes from Moniques Crepes or savor Mediterranean-inspired pressed sandwiches from Bikini Panini. Capture a memorable photo with a special guest at 110 Thompson Street—previous visitors have included Bluey, Princess Belle, and Queen Elsa. And don’t forget to grab some free popcorn and cotton candy from Ashland Dance Academy!

Show Your True Colors

In celebration of Virginia Pride, we encourage everyone to let their true colors shine. Dress in your brightest rainbow attire and show your pride as we come together to create a colorful, welcoming, and inclusive atmosphere. Whether you’re waving rainbow flags or sporting colorful accessories, let’s make this event a vivid display of unity and joy.

Art, Entertainment, and Community Spirit

Discover more artistic wonders with KandiMan’s original soft sculptures in front of Changing Reins, and browse Immagine LLC’s art outside Ashland Meat Company. Don’t miss Free to Read’s book giveaway outside the Ashland Branch Library. Engage in immersive games with RED VEIN Escape or delve into Ashland’s darker history with the Ashland Haunted History Tours.

Local restaurants and shops will stay open late, offering delicious farm-to-fork feasts and showcasing curated art and housewares, ensuring there’s something for everyone to enjoy.

Join the Celebration!

This final Ashland Fourth Fridays of the summer season is not just a community event; it's a celebration of inclusivity, pride, and local spirit. Bring your friends, family, and neighbors to experience a night of vibrant entertainment, diverse food, and a warm, welcoming atmosphere. Let’s celebrate our community, embrace our true colors, and make this a night to remember. See you in downtown Ashland!

Light Up the Tracks Events Guide

Downtown Ashland Virginia lit up with over 10 thousand lights during Light Up the Tracks

For the next six weeks, Ashland's holiday spirit shines bright with festive foods, events, and over ten thousand lights. We call the celebration Light Up the Tracks!

Here’s a sneak peek, and you can find the full calendar of events here.

Illuminated Events
Nov 18 - Light Up the Tracks Celebration with Downtown Ashland Association
Nov 18 - Illuminated Costume Contest at the Light Up the Tracks Celebration
Nov 19 - Olde Time Holiday Parade with the Ashland Kiwanis Club
Nov 19 - Thanksgiving Floral Arranging Workshop at the Hanover Arts and Activities Center
Dec 2 - Holly Jolly Holiday Party at the Ashland Theatre
Dec 3 - Deck the Halls at Pine Grove Farm
Dec 9 - Jolly Jaunt Bar Crawl & Concert With Origin Beer Lab
Dec 31 - Light the Way to 2024 at the Hanover Arts and Activites Center

Sleighing Shops
Dec 2 - Ashland Christmas Market
Dec 2 - England Street “Christmas Market” at Thrill of the Hunt
Nov 25 - Small Business Saturday in Downtown Ashland
Mon - Sat - Ashland Feed Store
Tues - Sat - Caravati's Architectural Salvage
Tues - Sun - Center of the Yarniverse
Tues - Sat - Changing Reins
Mon - Sun - Fin & Feather Pet Center
Mon - Sun - Hickory Creek Antiques
Tues - Sun - ReFunkIt
Tues - Sat - Thrill of the Hunt
Mon - Sun - Tiny Tim's Toys & Trains
Sat - The Shop at 112
Tues - Sat - Wagner Jewellers

Glow Shows
Every Saturday! - Caroling in Downtown Ashland
Weds - Sun - Fearfully Festive Escape Room at RED VEIN Escape
Fri - Sat - “Ghosts of Christmas Past” with Ashland Haunted History Tours
Fri - Sat - Live Concerts at Huddle Up Sports Bar
Fri - Sun - Ashland Museum & the Red Caboose Tours
Dec 1 - The Barter Players’ “Frosty the Snowman” at Ashland Theatre
Dec 1 - 3 - LUX Holiday Spectacular at Randolph-Macon College
Dec 3 - Richmond Symphony at Randolph-Macon College
Dec 7 - Choral and Instrumental Winter Concert with Randolph-Macon College
Dec 8 - 17 - “The Polar Express” at the Ashland Theatre
Dec 10 - Holiday Concert at Duncan Memorial United Methodist Church
Dec 10 - “The Grinch” at the Ashland Theatre
Dec 15 - “National Lampoon's Christmas Vacation” at the Ashland Theatre
Dec 21 - “It’s a Wonderful Life” at the Ashland Theatre

Festive Foods
Nov 23 - Thanksgiving Dinner at the Henry Clay Inn
Fridays - Wine Tasting at the Caboose Market and Cafe
Thursday to Monday - Dining at the Henry Clay Inn
Mon - Sat - Andy's Restaurant & Lounge
Mon - Sun - Ashland Meat Company at Cross Brothers
Wed - Sat - Ashland Pot Pie Company
Mon - Sun - Ban Thai
Mon - Sat - The Caboose Market & Cafe
Mon - Sun - Casa Herradura Family Mexican Restaurant
Mon - Sun - The Depot
Tues - Sat - Homemades by Suzanne
Wed - Sat - Huddle Up Sports Bar
Mon - Sun - Iron Horse Restaurant
Mon - Sun - Jake's Place
Tues - Sun - Origin Beer Lab
Mon - Sun - Sports Page Bar & Grill
Tues - Sat - Sugar Fix Bakery
Mon - Sun - SweetFrog
Mon - Sun - Trackside Kitchen and Wine

Ashland Halloween’s Wicked Long Weekend of Events

🎃Trick or treat yo’ self to a wicked long weekend of eerie-sistible events this Ashland Halloween.👇 See our highlight list below, and access the full calendar here.

Friday, October 27

🍹 Halloween Margaritas at Casa Herradura Family Mexican Restaurant
🍷 Wicked Wine Tasting at Caboose Market & Cafe
🍻 Adult Trick-or-Treat Bar Crawl with Iron Horse Restaurant, Origin Beer Lab, The Caboose Market & Cafe, and Trackside Kitchen and Wine
👻 Spirits of Railroad Avenue by Ashland Haunted History Tours

Saturday, October 28

🍺 Off the Rails Craft Beer Festival at the Hanover Arts and Activities Center
🌻 Ashland Farmers Market
🐮
Farmview Creamery at Jessica Roberston’s Studio
🧙‍♀️ Hocus Pocus at the Ashland Theatre
🎃 Halloween at the Ashland Museum
🦇 Bats at the Library in the Ashland Branch Library
🎭 The Rocky Horror Picture Show with a shadow cast at the Ashland Theatre

Sunday, October 29
🍳 Harvest Brunch at The Depot
🥂 Hard Cider on Tap at Origin Beer Lab
😱 Phobia at RED VEIN Escape
💀 The Nightmare Before Christmas screening at St. James the Less Episcopal Church

Monday, October 30
🍹Halloween Margaritas at Casa Herradura Family Mexican Restaurant
🍗 Eerily Cool Special on Hot Wings at Ashland Sports Page
🍁 Sale on Antique and Vintage Fall Decor at Hickory Creek Antiques
🎥 Halloween screening at the Ashland Theatre

Tuesday, October 31

🗺️ Kids Trick-or-Treat and Scavenger Hunt hosted by Downtown Ashland Association
🍬 Candypalooza Lane hosted by New Community Church in the Caravati’s Architectural Salvage parking lot
🎃 Halloween at the Center

Ashland Fourth Fridays Finale

🌻Ashland Fourth Fridays’ finale is September 22. Fall for fine, culinary, and performing artists one last time…👇

Live entertainment:

🩰 5 PM Ashland Dance Academy’s junior dancers perform inside The Depot.

🎹 5 PM Generations Trio performs standards and clever covers of rock classics in a groovy jazz mode on the Ashland Town Hall Pavillion stage.

🎵6 - 8 PM Vexine brings bluesy, rollicking rock to the Ashland Town Hall Pavillion stage.

👢 7 PM Boot Scooters lead line dancing at Ashland Town Hall.

🏛️Ashland Museum tells the story of our town through historical artifacts, oral histories, biographies, and more.

👻 Ashland Haunted History Tours reenacts the haunted history of our Victorian town.

🐇 RED VEIN Escape challenges guests to puzzling games.

🎥 Ashland Theatre shows a movie at 7 PM.

Eat and Drink:
🍜 Ban Thai Restaurant dishes out authentic Thai tea and cuisine for carryout.

🥘 The Henry Clay Inn provides dine-in options inside the historic space. 

🍺 Origin Beer Lab pours craft brews inside, on the patio, and in their beer garden.

🥘 The Iron Horse Restaurant serves seasonal elevated southern cuisine on the patio.

🥘 The Caboose Market & Cafe pairs beers and wine with farm-to-table meals indoors and out.

🥘 Ashland Meat Co. At Cross Bros serves up sandwiches, salads, ice cream, and beverages indoors and out.

🥘 The Depot serves pizza and libations with three art vendors on display and a 5 PM performance by Ashland Dance Academy.

🥘 Trackside Kitchen and Wine shows off their renovated space with all-American meals.

🍨 Sweet Frog lets you make your own frozen yogurt dreams come true.

🍹 Casa Herradura Family Mexican Restaurant offers a can’t-miss margarita special on the patio or in the expanded dining room.

🥘 Huddle Up Sports Bar is the destination for a giant dance floor, drinks, and dining.

🥘 Andy's Restaurant & Lounge’s homestyle plates pair perfectly with their outdoor patio and billiards. 

🍲 Tops China serves Chinese food favorites for dine-in or takeout.

Food trucks:

😋Hellenic Kouzina Greek Cafe brings authentic Greek cuisine to Ashland Town Hall 

🐷 RVA Outlaw Barbecue serves craft smoked meats that’ll make you squeel

🍦Sno Fields Shaved Ice keeps it cool with sweet snowballs and shaved ice

🥞Monique's Crêpes pulls up beside The Caboose Market & Cafe with their hand-crafted sweet and savory galettes.


Art:

📝ReFunkIt curates funk, handcrafted art, and gifts 

🏠The Shop at 112 is open to peruse posh antiques and collectibles shop.

🚂Tiny Tim's Toys & Trains features unique toys and games for ages 0 to 99.

🎨Ashland Dance Academy hosts Tinsel Hair and Face Painting inside 110 Thompson Street.

🪴 KP Jenkins Jewelry and Fine Arts on Town Hall Lawn creates jewelry inspired by nature.

🦙Meadowgate Alpacas on Town Hall Lawn offering items made from luxurious natural fibers.

🎨 Immagine', LLC on Town Hall Lawn produces art prints, stationery, and gift items.

🕯️Sweet Heat Candles repurposes stylish vessels to house soy candles.

🌊Cre8tdwseaglass on Town Hall Lawn designs nautical-inspired art from pure found sea glass. 

📸Julie Tashner Photography and Sassy Little Star Designs on Town Hall Lawn combine their love for photography and sewing.

👕 CreativeAfro, LLC on Town Hall Lawn brings a touch of African elegance to everyday style. 

🪵 Currier Turned on Town Hall Lawn has hand-turned wood bowls and accessories. 

🎨Lil' Bits of Whimsy on Town Hall Lawn hand paints magnets, ornaments, and cut paper art.

🐶Pawfect Sweets LLC inside The Depot serves us home-cooked food for Fido.

💋 Creations of A Kiss inside The Depot creates custom tumblers.

🪵Adam's Woodworking inside The Depot designs one-of-a-kind chopping blocks and cutting boards.

📝ErAlexica Cards Jewelry and Crafts inside The Depot delivers original cards and stationery.
 

🪴Part-Time Cryptid’s cute, nature-themed art is sold as buttons, art, and accessories on Robinson Street.

🐸 Toad Hill Goods on Robinson Street reclaims wood and linoleum block prints for handmade and homemade items.

💎a4ordablebeauty Jewelry Accessories, LLC on Robinson Street sells handcrafted jewelry for a bargain.

⛅️Heavenly Expressions by Crystal creates unique epoxy resin art on Robinson Street.

🧚‍♂️ The Curio Fairy makes magical creations to adorn and delight.

Huddle Up's Winter Concert Schedule

Huddle Up Sports Bar announces their winterful lineup of cozy concerts and events. With popular local bands headlining, Downtown Ashland is your destination for thaw-dropping dance parties!

The Winter Concert Series runs from November 23 to December 31, 2023. All shows begin at 8 PM with a $8-10 cover charge. Email huddleupinfo@gmail.com to reserve a table.

Friday, December 1, 8 PM
Double Down
A diverse group of seasoned musicians keeping classic and southern rock alive.

Saturday, December 2, 8 PM
Josh Duncan Band
Plays modern country for the Center of the Universe.

Thursday, December 7, 6:30 PM
K95 & The Boot Scooters
Come by for free line dancing, cold drinks, and giveaways.

Friday, December 8, 8 PM
LadySmyth
A rockin' band for music lovers. Covering all genres! Country, Rock, Motown, All Music!

Saturday, December 9, 8 PM
Tëaze
The tunes, moves, spandex, hair, and metal of the 80's.

Friday, December 15, 8 PM
Honky Tonk Heroes
Covering legends like George Jones and Willie Nelson to Nashville’s current kings like Jason Aldean and Luke Bryan, the Honkytonk Heroes play “Classic and Contemporary Country” from the past six decades.

Saturday, December, 15, 8 PM
Monkey Fist
Playing your favorite rock anthems from the 80's and the best of today's new rock!

Thursday, December 21, 6:30 PM
K95 & The Boot Scooters
Come by for free line dancing, cold drinks, and giveaways.


Sunday, December 31, 8 PM
En'Novation
En'Novation is made up of extremely well-seasoned singers and musicians that have decades of combined experience performing on the biggest stages of the eastern United States.

Don’t forget! Every Tuesday and Thursday
Huddle Up Sports Bar & Grill hosts Country Line Dancing from 7 - 10 PM.