What's happening across the Virginia Piedmont's wine country.
Peaches give way to apples and pumpkins at this family orchard that's been picking since 1954
Jenkins Orchards in Woodville has been a family-run pick-your-own stop since 1954, and come September its rows shift from peaches and plums to apples, pears, and pumpkins.
What the region's flagship wine celebration looks like, from the Monticello Cup judging to the Gold Medal Celebration at Boar's Head Resort
Monticello Wine Week culminates each fall in the Gold Medal Celebration at Boar's Head Resort, where the results of the Monticello Cup — the region's blind-judged wine competition — are unveiled to the public.
A free, self-guided October tour through the working farms and orchards behind Fauquier's food scene
The Fauquier Fall Farm Tour is a free, self-guided one-day tour each October organized by Fauquier County Agricultural Development, opening working farms across the county to visitors.
Inside the multi-vendor antique space anchoring Little Washington's back streets, from WWII memorabilia to vintage vinyl
Hazel River Arts & Antiques, a multi-vendor space at 12625 Lee Highway in Washington, VA, stocks fine antique furniture, WWII memorabilia, and vintage vinyl, and is open Thursday through Sunday, 10 a.m. to 5 p.m.
A small-batch brewery tucked in a B&B cellar, pouring unfiltered ales on a Main Street beer garden through fall
At 47 Main Street in Sperryville, The Brewery at Hopkins Ordinary pours unfiltered blonde ale, saison, and porter from a bed-and-breakfast cellar with a Main Street beer garden open Thursday through Sunday afternoons.
A farm winery and limited brewery on Elgin Drive pours Virginia wine and its own beer under one roof outside Luray
At Faithbrooke Barn and Vineyards outside Luray, The Vintage Barrel pours Virginia wine and its own limited-run beer, open Friday through Sunday with a 5.0 Google rating.
Live Piedmont blues at Eldon Farm honors Rappahannock's own legendary musician
The John Jackson Piedmont Blues Festival lands Saturday, September 26, 2026, at Eldon Farm at Clover Hill in Woodville, celebrating the Rappahannock-born blues legend with live music and cultural programming.
How to spend a September night in Rappahannock's smallest village, from cellar beer garden to schoolhouse dining room
Start in the cellar beer garden at The Brewery at Hopkins Ordinary (open Thursday–Sunday afternoons) and end a few steps away at The Black Twig Diner, open until 9 p.m. Friday and Saturday for farm-to-table dinner in the old Sperryville schoolhouse.
Where to launch, float, and take out along the South Fork this September and October
Cooler water and thinning crowds make September and October a quietly excellent stretch for paddling the South Fork Shenandoah, from Shenandoah River State Park's 5.2 miles of shoreline to the rough public ramp at Karo Landing.
Two working crossroads stores — one a gathering-place restaurant, one a garage-deli hybrid — that still anchor rural Rappahannock and Fauquier life
Orlean Market in Fauquier County and Settle's Grocery, Garage, Gas and Deli in Flint Hill are two working country stores worth a fall detour, both known for deli counters and gas pumps intact — though it's worth confirming current hours before you go.
Where to sleep after a day of farm touring and tasting rooms, from a historic manor stable to a vineyard cottage under Old Rag
Two vineyard cottages near Old Rag Mountain, a AAA Four Diamond manor circa 1840, and a Forbes Five-Star resort just over the county line anchor the region's fall lodging options this season.
Glass studios, a Downtown Mall consignment gallery, and a Front Royal botanical garden make for an unhurried September circuit through the Piedmont's quieter corners
Spend a September day moving between Veirs Studio Glass & Gallery in New Baltimore, the Consignment House Gallery on Charlottesville's Downtown Mall, and a quiet stop at Front Royal's Dr. Seide Memorial Botanical Gardens.
Main Street's beer-and-wine-garden gathering has drawn crowds downtown — confirm it's still running before you go
First Friday Warrenton has turned Old Town's Main Street into an evening gathering with a beer and wine garden and live entertainment — worth a call ahead to confirm it's still active.
A slow Saturday morning of local produce and a lazy paddle where the James bends through Albemarle
Scottsville Farmers Market runs Saturdays 9 a.m. to 1 p.m. at the town pavilion through November, and James River Runners keeps its outfitting operation open daily 8 a.m. to 6 p.m. for a fall float.
A Sunday morning in The Plains pairs studio glass with produce stands under the green barns -- if the market is still running
Unverified intel suggests Seldom Realms Glassworks will bring a booth of studio glass art inside the barn at Archwood Green Barns Farmers Market this Sunday, September 20, from 10am to 2pm -- worth a call ahead to confirm.
From a riverside boat landing to a small-town botanical garden, the low-key September stops that reward a slower drive through Front Royal and Luray
September's cooler mornings make this the season to walk the Dr. Seide Memorial Botanical Gardens in Front Royal or put a canoe in at Shenandoah River Park and Landing before the leaf-peeping crowds arrive.
Front Royal's Oktoberfest garden pours the seasonal favorite as fall color builds along the Blue Ridge
Vibrissa Beer has confirmed the return of its seasonal Falling Leaf Lager, pouring in the Not Your Average Oktoberfest Garden for Festival of Leaves weekend, October 10 and 11, 2026.
A possible Seldom Realms Glassworks pop-up at the Sunday market in The Plains, plus a call-ahead note before you go
Archwood Green Barns Farmers Market has long drawn shoppers to its distinctive green barns on Sunday mornings, with word of a possible Seldom Realms Glassworks pop-up this weekend — but it's worth calling ahead to confirm before you make the drive.
A recent hours-listing change has some visitors double-checking before they drive to Page County — here's what's actually confirmed for fall 2026
Luray Caverns keeps its cave at a constant 54°F and, per its posted hours, is open daily from 9am to 7pm this September — worth confirming directly given a recent hours update.
Four decades of mid-century furniture and original art make this Downtown Mall fixture worth a call ahead this fall
For more than 40 years, Consignment House Gallery has anchored Charlottesville's Downtown Mall with mid-century furniture and original art — though it's worth calling ahead, since recent activity has been quiet.
Blend-your-own classes and farm stays in a boutique tasting room near Little Washington
Skyline Vineyard at 65 Clark Lane in Washington, VA runs a wine blending lab and farm-stay lodging, open Thursday through Sunday just down the road from Little Washington.
Skip the caverns crowds for a slower Warren County afternoon among garden beds and mid-century finds
A slower alternative to the caverns crowds: an afternoon at Dr. Seide Memorial Botanical Gardens on E 8th Street, followed by a stop at a South Fork river landing before dinner — with a heads-up to confirm details before you go.
The Robinson and Conway Rivers offer cool, clear wild-trout water below Old Rag as the Blue Ridge turns color
The Robinson River runs stocked and native trout water out of Syria and Criglersville, while the Conway forms the Madison-Greene line through the Rapidan Wildlife Management Area — both fish coolest and clearest in fall.
An urban-style tasting room on a former spy base where visitors can blend and bottle their own wine
At Vint Hill Craft Winery in Fauquier County, visitors don't just taste wine—they blend and bottle their own, open daily except Monday and Tuesday, noon to 6 or 7pm.