England Street Christmas Market
2025-12-06 11:00 - 16:00 (America/New_York) | Thrill of the Hunt, 315 England Street, Ashland, VA, 23005, United States
The England Street Christmas Market, presented by Thrill of the Hunt, opened its courtyard gates in 2020. This seasonal market brings you curated handmade goods by local Crafters, Makers, and Artisans. Head down to England Street to explore and discover a casual quaint outdoor shopping experience, nestled at the entrance to Downtown Ashland.
*** For more information on this event click here. ***
Looking for a local dining option while in town for England Street Christmas Market? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Christmas at the Abbey
2025-12-07 14:00 - 16:00 | Hanover Tavern, 13181 hanover courthouse road, hanover, VA, 23069, United States
Join Hanover Tavern for a magical journey back in time to the era of Downton Abbey at our exclusive Holiday Tavern Tea event. Immerse yourself in the aristocratic charm of the Granthams as you savor a decadent three-course menu featuring savory sandwiches, freshly baked scones, and delightful sweets, all paired with a selection of traditional English teas and a special themed tea flavor
*** For more information on this event click here. ***
Looking for a local dining option while in town for Christmas at the Abbey? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Holiday House Tour
2025-12-07 14:30 - 17:30 | The Ashland Museum, 105 Hanover Ave, ashland, VA, 23005, United States
The Ashland Museum will offer two homes to tour on S. Center St on Sunday, December 7. Both houses will be open with a reception to follow.
*** For more information on this event click here. ***
Looking for a local dining option while in town for Holiday House Tour? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Winter on the Green
2025-12-13 17:00 - 20:00 | Historic Hanover Courthouse Complex, 13182 Hanover Courthouse Road, hanover, VA, 23069, United States
Celebrate the magic of the holidays at this heartwarming community tradition, Winter on the Green!
*** For more information on this event click here. ***
Looking for a local dining option while in town for Winter on the Green? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Ashland Holiday Market 2025
2025-12-20 09:00 - 12:00 | Downtown Ashland
The Ashland Holiday Market 2025 is the last Farmer’s Market in 2025. Find food, gifts, and craft items for your holidays, all locally made and grown within 30 miles of Ashland, VA. Live music will be at the pavilion and many familiar faces.
*** For more information on this event click here. ***
Looking for a local dining option while in town for the Ashland Holiday Market 2025? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Clear the Shelter Christmas Open House
2025-12-20 11:00 - 14:00 | Hanover County Animal Shelter, 12471 taylor complex lane, ashland, VA, 23005, United States
Let’s bring the magic of Christmas to the shelter and give these animals the love and help they deserve this holiday season. Head down to the Hanover animal shelter to pick out a new addition to your family!
For more information on this event click here.
Looking for a local dining option while in town for the Clear the Shelter Christmas Open House? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! Call us at 804-798-3100.

Caroling in Downtown Ashland
2025-12-20 16:00 - 17:00 | Downtown Ashland
Step into a storybook Christmas in the Center of the Universe! Downtown Ashland’s Light Up the Tracks brings old-fashioned holiday charm to life every Saturday from 5–7 PM, with festive carolers, sing-alongs, and seasonal cheer that will warm your heart.
*** For more information on this event click here. ***
Looking for a local dining option while in town for Caroling in Downtown Ashland? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Holiday Centerpiece Workshop
2025-12-21 14:00 - 16:00 | James River Cellars, 11008 Washington Highway, Glenn Allen, VA, 23059, United States
Join us for our Holiday Centerpiece Making Workshop at James River Winery! All will be merry and bright as we create this floral design that includes a beautiful lined wooden box that can be reused in the future once you learn to create floral displays with it.
*** For more information on this event click here. ***
Looking for a local dining option while in town for Holiday Centerpiece Workshop? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.

Christmas Eve Dinner
2025-12-24 16:00 - 22:00 | The Henry Clay Inn, 114 N Railroad Ave, Ashland, VA, 23005, United States
As Christmas Eve settles softly over Ashland, The Henry Clay Inn glows with the promise of a night meant to be savored.
Within these historic walls, the season invites you to slow down, gather close, and enjoy an evening shaped by warmth, tradition, and quiet indulgence.
Join us for a Special Christmas Eve Dinner, thoughtfully prepared for the holiday and served in the timeless comfort of the Inn.
Special Christmas Eve Dinner
4:00 PM – 10:00 PM
Before or after dinner, the Lounge offers a place to linger a little longer.
A well-poured drink, low light, and the easy hum of a winter evening.
The Lounge
3:00 PM – 11:00 PM
For those wishing to know what awaits on the menu, we invite you to explore further.
Click here for information

Christmas Day Brunch
2025-12-25 10:00 - 15:00 | The Henry Clay Inn, 114 N Railroad Ave, Ashland, VA, 23005, United States
Christmas Day at The Henry Clay Inn unfolds at an easy, unhurried pace. Morning begins quietly, the day stretches long, and the glow of the season carries from sunrise to nightfall.
Midday invites guests to gather for a Special Christmas Day Brunch, created for the season and meant to be lingered over.
Special Christmas Day Brunch
10:00 AM – 3:00 PM
As evening arrives, Dinner continues with our current menu, while the Lounge remains open for those who prefer to let Christmas linger just a little longer.
Dinner
4:00 PM – 10:00 PM
The Lounge
3:00 PM – 11:00 PM
For those wishing to know what awaits on the Brunch menu, we invite you to explore further.
Click here for information

New Year's Eve Dinner
2025-12-31 16:00 - 22:00 | The Henry Clay Inn, 114 N Railroad Ave, Ashland, VA, 23005, United States
As the year draws to a close, The Henry Clay Inn welcomes guests to an evening of celebration, warmth, and reflection.
Within these historic walls, the night sparkles quietly, inviting you to pause, gather, and savor the moment.
Special New Year’s Dinner
4:00 PM – 10:00 PM
Before or after dinner, the Lounge offers a place to linger with a drink in hand, letting the last hours of the year unfold at their own gentle pace.
The Lounge
3:00 PM – 11:00 PM
For full details on New Year’s Eve Dinner Menu
click here for more information

Annual Pokebash Card Show
2026-01-03 10:00 - 18:00 | Hanover Academy, 117 Frances Rd, Ashland, VA, 23005, United States
Get ready for the annual PokeBash Card Show! Our one year anniversary Bash will take place where it all started, Ashland Virginia! This event will be held at the spacious Hanover Academy and will feature 105 tables of TCG Action! Pikachu will make an appearance for a free Meet and Greet! All ages are welcome.
*** For more information on this event click here. ***
Looking for a local dining option while in town for the Annual Pokebash Card Show? Be sure and make reservations at The Henry Clay Inn for brunch or dinner! We offer porch or indoor dining. Call us at 804-798-3100.
