Thankful in the Valley: Winchester Then & Now 🦃📜

Winchester Wire #033: A Civil War Thanksgiving letter, Windependent Weekend, events and happenings and more.

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Winchester Wire
November 26, 2025

Happy Thanksgiving, Winstigators!

Winchester was founded in 1744, well before Thanksgiving was declared a national holiday. Early settlers from England, Ireland, Scotland, and Germany held what they called “harvest Thanksgivings” or “Harvest Home” celebrations. These events weren’t tied to a specific date, but they were tied to the agricultural cycle and revolved around church based days of prayer followed by community meals and celebrating the successful season of crops.

Moving ahead to October 3rd, 1863 (smack in the middle of the Civil War), Abraham Lincoln declared a national Thanksgiving to be held on November 26th. Lincoln’s motivations were straightforward: boost morale during the war by pointing to recent Union victories in Vicksburg and Gettysburg as signs of God’s will and to have a shared national observance for the first time. Before Vicksburg and Gettysburg, the Union had been suffering years of setbacks, heavy losses and high casualty totals leading to low morale, dwindling enlistment totals and wavering support.

Lincoln’s declaration for a national Thanksgiving was unprecedented; he asked all states to pause the war on the same day and he changed the scattered, regional Thanksgivings to one united holiday. In short, Thanksgiving was designed to steady the nation emotionally and politically.

But in Winchester, the meaning of that first Thanksgiving was much more complicated. During the Civil War, control of Winchester changed all the time between the Union and Confederate forces, sometimes multiple times in a week. A change of hands for Winchester could mean full military occupation, a retreat that left the town to the other side or a cavalry raid that took control temporarily. Winchester was the gateway to the Shenandoah Valley and both sides wanted it; all told there were over 70 different times Winchester changed hands during the war.

What’d that mean for residents here during that time? It was a revolving war-zone and flags and loyalties were changing constantly; families would keep both Confederate and Union flags and fly the appropriate one depending on who had control of Winchester at any given moment. Supplies were seized by the Union or the Confederacy all the time, and wounded soldiers were filling up local churches and homes.

When Lincoln declared the first Thanksgiving, Winchester was under Union control, but many families still had strong ties to the Confederacy. While Lincoln had declared the first Thanksgiving as some sort of divine intervention, the Confederate loyalists felt that Thanksgiving was more political and quietly avoided observing it altogether. It was only after the war that the people of Winchester began to see Thanksgiving as a shared day of gratitude.

To give you a deeper idea of what Thanksgiving was like in Winchester for someone in the war, correspondence from a Union soldier named Samuel E. Nichols exists in the Library of Congress.

Nichols, a lieutenant with the 37th Massachusetts, woke up on Thanksgiving morning in 1864 here in Winchester, one year after the first official holiday. He had been stationed here since September when the Union forces had won the Third Battle of Winchester.

His letter to his family at home reads:

Hd Qrs. 37th Mass. Vols. Opposite Co. Ho. Winchester, Va. November 27, 1864

Dear Folks at Home,

I will tell you how I passed Thanksgiving, with the hope that I can get the same indulgence from you. The morning of the 24th day of November, 1864, dawned beautifully upon the civilians and soldiers occupying that lovely country seat, Winchester, Va.

Starting wildly from our slumbers at the unearthly sound of “Reveille”, which is sounded within a few rods of these headquarters, we found ourselves with an appetite adequate for the occasion and fully equal to that usually demanded on that auspicious and chicken-stuffed day. Breakfast passed with a reasonable consumption of food adapted to the day, reserving our main and reliable forces of capacity for the terrible onset upon turkeydom in general at about two o’clock p.m. After breakfast the guard must be mounted as usual, which was attended to, as business precedes pleasure, in military as well as civil matters. After that a reasonable amount of beer was attended to, the unreasonable part not taken. Something seemed to whisper to me all the forenoon “Sam, you better get your dinner early or you may lose it”. You may rest assured that I always hearken to such messages from the spirit land and I sent word to have dinner at one o’clock.

At one o’clock, therefore, I dined with three of my companions. I will not enumerate all the dishes we enjoyed, but suffice it to say we all ate a sufficiency and had a good time. As I was returning to the office at two o’clock an order was handed in to the comdg. officer of the Reg, nearly in these words: “You will have your command in readiness to move at a moment’s notice in light marching order.” In five minutes another order came as follows: “Sir: You will move your command in light marching order, out on the Berryville pike and report to Col. Kellogg, who commands the expedition.”

In about ten minutes we were moving at quick step. Our regiment was the only infantry going out. The rest was cavalry. We marched nearly east, without halting till six o’clock, when we received orders to countermarch and report to Winchester, which we did, reaching there about nine o’clock and some later.

We were hungry, I tell you. As the Actg. Adg’t. I had a horse to ride which made it much easier for me, although before we got back, it was pretty cold riding. But Moseby kept out of our way.

Soon after we got in, I went to bed and to sleep. Thus went off my Thanksgiving. Since then nothing exciting. A review of our forces here at the Post took place day before yesterday.

With much love, Saml. E. Nichols

I have not postage stamps, so I frank my letters

First page of letter, Samuel E. Nichols to his family, November 27, 1864. Samuel E. Nichols Correspondence, Manuscript Division, Library of Congress.

In the 1920s, the letters of Samuel Nichols were compiled and published in a book that you can read online here.

So if your turkey runs late or the rolls burn, just remember at least nobody is ordering you to “move at a moment’s notice in light marching order” over to Berryville Pike!

Windependent Weekend!

There’s a lot happening around town this weekend, but I wanted to take a moment to highlight Windependent Weekend. It’s a three-day celebration of Winchester’s independent spirit, showcasing local shops, makers, restaurants, and artists. Downtown businesses are rolling out exclusive deals, pop-ups, and live events, encouraging both locals and visitors to support and shop small businesses. It’s part community festival and part small-business boost, so if you have a chance to swing by the Walking Mall, be sure to check it out!

Events and happenings in Winchester and the surrounding territories:

Friday, November 28th

Kimberly’s,Mckee’s & The Market, Winchester - Black Friday Doorbuster Deals and Champagne Brunch, 6 AM

War Memorial Park, Martinsburg - Christmas in the Park 🎄❄️✨, 5:30 PM

Theatre Shenandoah, Edinburg - A Christmas Story, 7:30 PM

American Legion Post 71 WV - Jackson-Perks, Charles Town - Public Night @ the Legion, 6 PM

Love Revival Church, Front Royal - Thanksgiving Community Dinner, 7 PM

Bried Family Vineyards, Clear Brook - Wine Trivia Night at Briedé Family Vineyards, 6 PM

The Black Twig, Sperryville - HOMECOMING 2025 🎵 LIVE DJ 🎶, 7 PM

Bridgeway Bikes, Brunswick - Bicycle Scavenger Hunt, 12 PM

The Garage on King, Martinsburg - Trivia Friday’s, 6 PM

Stone Tower Winery, Leesburg - Holiday Market, 11 AM

Box Office Brewery, Strasburg - Shockwave Band, 7 PM

Elmwood Farm Bed and Breakfast, Williamsport - Elmwood Farm Bed and Breakfast Market Fair, 9 AM

Barn of Harpers Ferry, Harpers Ferry - Lillian Hackett, 8 PM

Styled by Sweetface, Stephens City - Black Friday @ Styled by Sweetface, 10 AM

Winchester Little Theatre, Winchester - A Christmas Carol at Winchester Little Theatre, 8 PM

Another Turn and Tack Apparel, Purcellville - Black Friday Sale, 10 AM

The Old Lucketts Store, Leesburg - Lucketts Holiday House November 28th-30th, 10 AM

Clearbrook Park, Clear Brook - Walking in a Winter Wonderland

Chilly Hollow Brewing Company, Berryville - Chilly Hollow's First Anniversary and our 101st show!, 1 PM

Old Town Winchester Walking Mall, Winchester - Windependent Weekend, 10 AM (all weekend)

Saturday, November 29th

Bright Box Theater, Winchester - Comedy Showcase 7 PM show and 9:30 PM show

Winchester Book Gallery, Winchester - Author Event: Helen Vettori - Black Swan Series, 2 PM

Bear Chase Brewing Company, Bluemont - Old World Christmas Market: Small Business Saturday, 11 AM

The Book Shelf, Winchester - Yule Luna Market 2025, 10 AM

Ranson Civic Center, Ranson - 2nd Annual Merry Scoutmas Craft Show, 11 AM

Winchester Brew Works, Winchester - Holiday Market & Big Schloss Release Day!, 2 PM

Hagerstown Model Railroad Museum, Hagerstown - Fall Model Train Sale, 9:00 AM

Broadlands Village Center, Ashburn - Santa and Carriage Rides!, 4 PM

Tally Ho Theater, Leesburg - Herr Metal, 7 PM

Charles Washington Hall, Charles Town - The Market at CW Hall Featuring The 1786, 10 AM

The Conche, Leesburg - Art Of Cocktail Making Class, 12 PM

Shenandoah Valley Axe Throwing Co, Front Royal - Karaoke & Free Music Bingo, 6 PM

Winchester Moose Lodge 1283, Winchester - Winchester Moose Lodge 1283, 7 PM

On Cue Sports Bar & Grill, Front Royal - The Punky Brewsters Live at On Cue!!, 8 PM

Mecklenburg Inn, Shepherdstown - Glib & Sunniva @ The Mecklenburg Inn, 9 PM

Notaviva Farm Brewery & Winery, Millville - Notaviva Songwriter Showcase, 6:30 PM

Interchange Tiki Bar & Brewery, Williamsport - Moe Stringz @ Interchange Tiki Bar & Brewery, 6:30 PM

Four Seasons Books, Shepherdstown - Small Business Saturday @ Four Seasons Books, 10 AM

West Oaks Farm Market, Winchester - West Oaks Holiday Craft Show, 9 AM

Simply Divine Home Decor & Boutique, Martinsburg - Small Business Saturday Vendor Pop Up, 9 AM

Sunday, November 30th

Typewriter Studio, Winchester - Holiday Card Making, 4PM

Old Farm Winery at Hartland, Aldie - Holiday Vendor Fair, 12 PM

The Catamount Lounge, Front Royal - Tarot Night, 5 PM

Gathering Springs Farm, Sam Fred Road, Middleburg, VA, USA, Middleburg - Holiday clay tree making at Gathering Springs, 2 PM

Bear Chase Brewing Company, Bluemont - Selfies with Santa & Tree Lighting, 1 PM

Four Seasons Books, Shepherdstown - Artists Sunday @ Four Seasons Books, 11 AM

Barrel Oak Winery and Brewery, Delaplane - Sundays at Barrel Oak Winery and Brewery, 11 AM

Haley Willingham Photography, Shepherdstown - Santa Mini Sessions, 10 AM

Archwood Green Barns Farmer's Market, The Plains - Archwood Green Barns Farmers Market, 10 AM

Echelon Wine Bar, Leesburg - Pinot Noir Showdown: Oregon vs Burgundy, 3 PM

Museum of the Shenandoah Valley, Winchester - Museum Store Sunday, 10 AM

Stockyard Brewery, Lovettsville - Santa, Steer & Sodas, 1 PM

Wild and Wonderful Play Cafe, Ranson - Trunk of Cheer, 2 PM

Good Spirits Tree Farm, Hagerstown - Opening Weekend 2025, 10 AM

Historic Rosemont Manor, Berryville - Christmas Open House, 3 PM

Wolf Gap Vineyard & Winery, Edinburg - Dylan Woelfel at Wolf Gap Vineyard, 2 PM

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Have fun out there!