Culpeper Pull-Up: Your Oct 16–18 Weekend Guide

Hey neighbor,

Fire up the smokers, Culpeper. Hop N' Hog rolls into the Depot on Saturday with a people's-choice BBQ competition, bourbon and craft beer tastings, and two live bands. Out at Mountain Run Winery, 40+ local crafters, live music, and three food truks turn the Fall Festival into an all-day hang. It's also your last shot at an apple butter donut: Graves Mountain's Apple Harvest Festival wraps its final weekend up in Syria. And Friday night, the kids get a head start on Halloween at the Braggs Corner Trunk or Treat. Grab your calendar — we're pulling up.

— J. Patrick

Hop N' Hog Block Party & BBQ Competition
Saturday, October 17 | 12:00–5:00 PM 📍 The Depot, 111 S Commerce St

Culpeper Renaissance's fall block party is the highest-energy afternoon on the downtown calendar. You're the judge in the people's-choice BBQ competition, then you work your way through craft beer, wine, cider, and bourbon tastings while artisan vendors line the Depot District.

Hometown openers Smiling Politely take the stage from noon to 1:30, then Goodtime Alibi plays 2–5 PM. Kids 16 and under get in free. Adult tickets come in Backyard, Pitmaster, Bourbon Boss, and VIP tiers, so check the event page for pricing and grab yours before they're gone.

If you're here → go eat here. Mountain Run Winery has the weekend's confirmed truk lineup. No other touring truks have logged Culpeper stops for Oct 16–18 yet, so check Trukfoo before you head out.

Saturday, October 17

🍔 Pepper's on the Go @ Mountain Run Winery, 10753 Mountain Run Lake Rd, 12–7 PM — confirmed by the winery (burgers, chicken tenders, and more)

🍗 Over the Top Chef @ Mountain Run Winery, 10753 Mountain Run Lake Rd, 12–7 PM — confirmed by the winery

☕ Travelin Tom's @ Mountain Run Winery, 10753 Mountain Run Lake Rd — confirmed by the winery (coffee and sweet treats)

🐷 BBQ competitors + food vendors @ Hop N' Hog, The Depot, 111 S Commerce St, 12–5 PM — vendors not named yet

🍎 Apple butter donuts, apple pies & homemade ice cream @ Graves Mountain Apple Harvest Festival, 205 Graves Mountain Ln, Syria, 10 AM–4:30 PM — confirmed by the farm

🍺 Weekend food truk @ Old Trade Brewery & Cidery, 13270 Alanthus Rd, Brandy Station — unconfirmed, based on the regular weekend pattern

Sunday, October 18

🍎 Festival food & fresh cider @ Graves Mountain Apple Harvest Festival, 205 Graves Mountain Ln, Syria, 10 AM–4:30 PM — confirmed by the farm

👉 Want the full, always-updated schedule? Head to trukfoo.com to see every truk's stops in real time.

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Central Virginia / Richmond

Saturday, October 17 | 10:00 AM–6:00 PM & Sunday, October 18 | 11:00 AM–5:00 PM 📍 Rassawek Vineyard, 6276 River Rd W, Columbia (Goochland)

The 6th annual Rassawek weekend mixes a full pro rodeo (1–3 PM, bull riding included) with blacksmiths, chainsaw carving, sawmill demos, antique tractors, a petting zoo, pumpkin decorating, live music, and local food, wine, and beer. Rodeo admission is included with your festival ticket; prices go up after Friday, Oct 16.

Charlottesville

Saturday, October 17 & Sunday, October 18 | 9:00 AM–5:00 PM 📍 Drumheller's Orchard, 1130 Drumheller Orchard Ln, Lovingston

About 40 minutes south of Charlottesville in Nelson County, this family orchard throws a two-day harvest party with live music, local vendors selling food and crafts, apple picking, and hot donuts with cider. Admission isn't listed, so check before you go.

Northern Virginia

Saturday, October 17 | 2:00–5:00 PM 📍 Dillon's Woods, 221 S Nursery Ave, Purcellville

Purcellville's town-wide fall celebration wraps up with an afternoon party in Dillon's Woods, the shady grove at the historic Fireman's Field complex in western Loudoun. Bring your festival passport for the prize drawing; you must be present to win.

Hampton Roads / Virginia Beach

Saturday, October 17 | 10:00 AM–5:00 PM & Sunday, October 18 | 12:00–5:00 PM 📍 Stockley Gardens Park, Ghent, Norfolk

A Norfolk tradition since 1984: 125+ artists from across the country set up in a garden park in historic Ghent, with live music, kids' activities, and food vendors. Free to attend, and every dollar raised supports Hope House Foundation's work with people with intellectual and developmental disabilities.

Shenandoah Valley

Friday, October 16 | 3:00–9:00 PM, Saturday, October 17 | 10:00 AM–7:00 PM & Sunday, October 18 | 10:00 AM–5:00 PM 📍 North Mountain Vineyard & Winery, 4374 Swartz Rd, Maurertown

A medieval faire set on a Shenandoah County vineyard, with mead, wine, and beer flowing and proceeds supporting breast cancer awareness. Can't make it this weekend? It returns October 23–25. Get tickets here.

That's the lineup, Culpeper. Whether you're judging ribs at the Depot, shopping crafters at Mountain Run, or grabbing one last apple butter donut at Graves Mountain — get out there and live it. Downtown doesn't slow down, and neither should you.

See you next weekend.

Pull up soon,
J. Patrick

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The Pull-Up is your weekly guide to food truks, festivals, local events, and hidden gems in Culpeper and beyond. Published by FestiveFly. Written by J. Patrick.