Oct 22 Thursday
Jazz in the Park is an annual summer concert series featuring a different top quality professional jazz group on Thursdays 7-9 pm at the Bandstand in Gypsy Hill Park in Staunton Va. This 2026 summer season runs July 9 - Sept. 3. Concerts are Free & open to the public, held rain or shine. Concessions are available. Some bench seating available in front of the bandstand; lawn chairs/ blankets recommended to stretch out comfortably in this lovely park seating under the trees. Family friendly. Come out & enjoy all the great music this summer! 🎶For more info call or TEXT : 540-280-4321
Don’t miss Grace & Glorie, Oct. 9-Nov. 8. The poignant, heartwarming comedy by acclaimed Virginia playwright Tom Ziegler explores love, loss, and the universal search for meaning in all our lives. Grace, a fiercely independent 90-year-old with terminal cancer, checks herself out of the hospital to spend her final days at her rustic cabin home nestled deep in the breathtaking Blue Ridge Mountains. Glorie, a Harvard MBA, is searching for a new purpose in her life and hoping to find peace in Appalachia, far from the demands of New York City. She volunteers for her local hospice program. Her first client is Grace. What begins as the hilarious collision of two opposite cultures and generations turns into a rich and abiding friendship, in which each woman finds her home. Filled with humor, heart and hope, Grace and Glorie is a celebration of the transformative power of human connection, and a tribute to the strength and resilience of women and their friendships at any age. Starring Richmond favorites Catherine Shaffner* and Amber Marie Martinez. (*Member, Actors' Equity Association)
Oct 23 Friday
Medicare Advantage or Part D plans change every year. Medication coverage and costs, premiums, deductibles, and provider networks may all be different next year - even if you make no changes. Stay in control by reviewing options during Open Enrollment.
JABA offers FREE, unbiased counseling from certified volunteers. Choose a plan that will best cover your medications and save you money. Understand your options. Make an informed decision. Request an Appointment: (434) 817-5248 or jabacares.org/medicare-counseling
The Botetourt County Historical Society, Inc. and Historic Fincastle, Inc. invite visitors to experience the darker side of Fincastle's past as the annual Haunted History Walking Tour returns this October.
Each year brings an entirely new tour, and 2026 is no exception. This year's event features a fresh collection of stories drawn from local history, long-forgotten legends, and mysterious tales that have lingered in Fincastle for generations. As guests stroll the town's historic streets by lantern light, costumed interpreters will bring these stories to life at some of Fincastle's most iconic locations.
This year's tour features a fresh collection of stories inspired by local history, community lore, and the enduring mysteries that have surrounded Fincastle for generations. Some are rooted in documented events, others in stories passed from one generation to the next, and a few invite visitors to decide for themselves where history ends and legend begins.
Now a beloved fall tradition, the Haunted History Walking Tour attracts history lovers, paranormal enthusiasts, and families looking for a unique October evening. Whether you're returning for another year or joining us for the first time, you'll discover stories you may not have heard before.
Event DetailsDates: Friday, October 23 and Saturday, October 24, 2026
Times: Tours begin at 6:00 p.m. and depart every 30 minutes. The last tour leaves at 8:00 p.m.
Location: Tours begin at the Chamber of Commerce office
Tickets: $15 Adults | $10 Children (12 and under)Each guided tour lasts approximately 80 minutes. Participants are encouraged to wear comfortable walking shoes and dress appropriately for the weather. Tours are held rain or shine.Tickets will be available exclusively through Eventbrite.For more information and tour updates, follow the Botetourt County Historical Society and Historic Fincastle on social media or visit their websites.
Bringing his legendary humor, quick wit, and decades of entertainment experience to the stage, Jay Leno arrives at the Academy Center of the Arts on October 23 for an evening of stand-up comedy and unforgettable storytelling. From his iconic run as host of The Tonight Show to his acclaimed series Jay Leno’s Garage, Leno has become one of the most recognizable and celebrated voices in American entertainment.
Audiences can expect a fast-paced night of sharp observational comedy, hilarious personal anecdotes, and the effortless charm that has kept Jay Leno at the forefront of comedy for generations. Whether sharing stories from late-night television, life on the road, or his passion for classic cars, Leno delivers the kind of engaging live performance that leaves audiences laughing long after the curtain falls.
Oct 24 Saturday
Step UP for Down syndrome is our signature community awareness and fundraising event designed to bring the community together to show support and solidarity with individuals with Down syndrome. VDSA hosts 3 Step Up events across our service area, offering multiple locations and times of year for you to join us in Stepping UP to show your support for Down syndrome.
Celebrate Virginia Wine Month with the Virginia Museum of History & Culture’s fifth annual Virginia Vines wine festival on Saturday, October 24th. This year’s event will feature wine selections from some of Virginia’s best wineries and vineyards, live music, food trucks, demonstrations from Marshall Scheetz of Jamestown Cooperage, and after-hours access to the museum’s newest exhibition, Barbie™: A Cultural Icon.
Tickets Include:
Free evening admission to the museum, including access to Barbie™: A Cultural IconSamples from participating wineriesCommemorative tasting glassAccess to live music, food concessions, and demonstrations Featuring 5 Virginia wineries who are either owned/operated by women or have women wine makers: Common Wealth Crush Co., Rosemont Vineyards & Winery, Early Mountain Vineyards, Veritas Vineyard and Winery, and Blenheim Vineyards.