Mother’s Day Weekend
This is the weekend you’ve been waiting for. Blooms are out, temperatures are perfect, and wineries, cideries, and breweries across the region have pulled out all the stops for Mother’s Day weekend. Whether you’re planning a special dinner, a lazy afternoon on a vineyard patio, or a Saturday night with live music, there’s something here for every kind of celebration.
Featured Venue: Early Mountain Vineyards
Madison, VA · earlymountain.com
If you’re looking to truly impress this weekend, Early Mountain Vineyards in Madison is the place. Widely regarded as one of Virginia’s finest wineries, Early Mountain pairs world-class wines — crafted by winemaker Maya Hood White — with an elevated culinary program helmed by Chef Tim Moore and Chef de Cuisine Kristen Hall. Their kitchen draws from the best seasonal produce local farms have to offer.
This weekend Early Mountain is running two unmissable events:
Mother’s Day Prix Fixe (May 7–11) — Treat Mom to a multi-course seasonal menu paired with Early Mountain wines. Available all week with extended hours Sunday. Reservations strongly recommended. Book →
Early Mountain x Crimson Lane Winemaker Dinner (Saturday, May 9 at 6:30 PM) — An intimate evening bringing together two of Virginia’s standout producers. Winemaker Maya Hood White and Crimson Lane’s Dominick Fioresi guide the evening — sharing the vineyards, vintages, and decisions that shape each bottle. Space is extremely limited. Reserve →
Early Mountain Vineyards · 6109 Wolftown-Hood Road, Madison VA 22727
Friday, May 8
Kick off the Mother’s Day weekend right.
Music at the Vineyard: Gina Sobel — Jefferson Vineyards · 5–7 PM
Award-winning Jefferson Vineyards wines + live music among the vines. A classic Friday evening. Get details →
Friday Night Out: The Lonesome Millies + Half-Price Wine Flights — Ducard Vineyards · 5–8 PM
Rappahannock-based acoustic trio plays folk, Americana, and light rock. Wine flights are half price after 4 PM. Bring a picnic. Get details →
Sunset Music Series — Knights Gambit Vineyard · 5–8 PM
Free every Friday. Bring a chair or blanket. Wines by the glass + Potter’s hard cider. No reservations needed. Get details →
Boot Scoot Square Dance Party — Potter’s Craft Cider · 5:30 PM
YEEHAW. Square dancing at one of Charlottesville’s favorite craft cideries. Don’t miss this one. Get details →
Friday Sunset Soirée: Scuffletown + Arepas on Wheels — Chisholm Vineyards · 6–9 PM
The first Friday Soirée of the season. Acoustic duo Scuffletown plays roots, jazz, bluegrass, and originals. Arepas on Wheels food truck on site. 100% estate wine + Blue Ridge Mountain sunset views. Get details →
Mother’s Day Floral Arrangement Workshop — Hazy Mountain · 6–8 PM
Ciara guides you through creating your own spring floral arrangement. Perfect early Mother’s Day treat. Get details →
Virginia Oyster & Wine Celebration with Live Music — Eastwood Farm and Winery · 5 PM
Oysters + Virginia wine + live music. It doesn’t get more Friday evening than this. Get details →
Saturday, May 9
The biggest day of the weekend.
The Art of Growing Peonies Workshop — The Market at Grelen · 9 AM · Free, RSVP required
Free class from Grelen’s Gardening Education Series. Learn the art of growing peonies just in time for spring. Get details →
Bloom Girls Flower Pop-Up — The Market at Grelen · 9 AM
Buy Mom a fresh bouquet for Mother’s Day. The Bloom Girls bring beautiful flowers all weekend. Get details →
Rosé All Day — Afton Mountain Vineyards · 11 AM – 7:30 PM
All-day rosé tasting event at the stunning Afton Mountain Vineyards. Live music from Caravan of Fools at 4 PM. Get details →
Pop-Up Art Market — Blenheim Vineyards · 11 AM – 4 PM
Local artists and makers under the tent at Blenheim. Sip a glass while you explore and shop. Get details →
Spring Fling — Southwest Mountains Vineyards · 11 AM – 4:30 PM
Second annual spring celebration featuring the release of the 2025 Cuvée Rosé. Perfect Saturday afternoon. Get details →
Goat’s Milk Soap-Making Workshop — Merrie Mill Farm & Vineyard · 11 AM – 1 PM
Create custom goat’s milk soaps with florals, lavender, citrus, or botanical blends. Perfect Mother’s Day activity. Tickets: $35–$42. Get details →
Live Bold JeeperFest — Bold Rock Nellysford · 11 AM – 5 PM
Jeeps, hard cider, and mountain views. Bold Rock’s annual Jeep festival returns to Nellysford. Get details →
Early Mountain x Crimson Lane Winemaker Dinner — Early Mountain Vineyards · 6:30 PM
See featured venue above. Space is very limited — book now. Reserve →
Second Saturday: Scuffletown — Ducard Vineyards · 6–9 PM
Rollicking live music from Scuffletown. Marc’s smooth voice and Johnny’s multi-instrumental magic in the mountains. Get details →
Live Music in the Orchard: Her Checkered Past — Albemarle Ciderworks · 6:30 – 8:30 PM
Live music in the orchard at one of the region’s most beloved cider destinations. Get details →
Don’t Look Up — Bald Top Brewing Co. · 6–9 PM
R&B and rhythm from Staunton’s Don’t Look Up. Bald Top brings the energy. Get details →
Jeremy’s Ten: The Pearl Jam Tribute — Pro Re Nata Brewpub · 7–10 PM
The nation’s most authentic Pearl Jam tribute. GA tickets: $18 presale / $25 at the door. Get details →
Sunday, May 10 — Mother’s Day
Give Mom the day she deserves.
Mother’s Day Prix Fixe — Early Mountain Vineyards · All day, reservations recommended
The full multi-course experience with extended Sunday hours. Book ahead. Book →
Special Mother’s Day Brunch — The Market at Grelen · 9 AM
Special brunch menu + rosé discounts at this beloved botanical marketplace and nursery in Orange County. Get details →
Yoga at Hazy Mountain — Hazy Mountain · 11 AM – 12 PM
Start Mother’s Day with a grounding yoga session at the vineyard. Get details →
Mother’s Day Spring Pour — King Family Vineyards · 10 AM – 5:30 PM
Open regular hours with special Mother’s Day activities. One of the most scenic vineyards in the region. Get details →
Live Music: Sally Rose — Afton Mountain Vineyards · 11 AM – 5 PM
Mother’s Day live music all afternoon. Tasting room open 11–5 PM. Get details →
Mother’s Day at Bold Rock — Bold Rock Nellysford · 11 AM – 2 PM
Celebrate Mom with hard cider in the mountains. Get details →
Mother’s Day Market + Live Music: Vicky Lee — Eastwood Farm and Winery · 11 AM
Market, live music from Vicky Lee, and the farm’s beautiful setting. Get details →
Mother’s Day Brunch — Glass House Winery · 12 – 1:30 PM
Just 12 guests. One seating. Four courses by Chef Tim. $80 per person (tax and gratuity included). This is the intimate brunch of the weekend. Book →
Have a wonderful Mother’s Day weekend in wine country. — The Weekendr Team