Upcoming Events on the Trail
We can't wait to see you!
HARVEST 2026 INDIVIDUAL WINERY EVENTS ALONG THE TRAIL
September 12th, 2026 - 11:30am-1:30pm - Live Music Saturday with Josh Rosenblum at Four Sisters Ranch Vineyards & Winery
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September 26, 2026 - 6-10pm - 30th Anniversary Celebration at Locatelli Vineyards.
Live music by DV8, dancing, BBQ. TICKETS
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September 26, 2026 - 6:30 pm - New Orleans Style Dinner at Graveyard Vineyards. TICKETS
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September 26, 2026 - 5-8pm - Hot Summer Nights in San Miguel Car Show at Cinquain Cellars. Complimentary tastings and BBQ. For car show participation, email beth@cinquaincellars.com
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October 17, 2026 - 2-6pm - Pianetta Palooza - Live Music - Food by Cahoots - Cornhole Tournament - Wine & Good Times! TICKETS
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October 17, 2026 - 12-4pm - Harvest Wine Weekend Open House at Cinquain Cellars. Complimentary tastings and wine specials.
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October 24, 2026 - 11am - 4:30pm - Harvest Marketplace at Four Sisters Ranch Vineyards & Winery.
12-3pm: Live music with jazz, blues, and soul vocalist Sunny Wright, accompanied by guitarist Jacob Odell. Food Truck to be announced.
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November 6-7, 2026 - Rampart Ride Supporting EOD Warrior Foundation - Tackitt Family Vineyards. Ride for a cause - wine - food - music! MORE INFO
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November 21, 2026 - 12-4pm - Pre-Thanksgiving Open House at Cinquain Cellars.
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December 12, 2026 - 12-3pm - Holiday Open House at Four Sisters Ranch Vineyards & Winery. Complimentary treats - live piano music by Eric Burgener (12-2) - gift vendors - wine specials and discounts.
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Harvest Bingo Along the Trail October 1-27, 2026
During Harvest Wine Month, explore the wineries of the Pleasant Valley Wine Trail and experience the excitement of harvest! Complete a Bingo Board, available at participating wineries, and submit for a chance to win a $100 VISA gift card. Chat with a winemaker, photograph a grapevine, meet a winery dog! Bingo!
Cans 4 Cabs Holiday Food Drive - November 1-22, 2026
Help support families in need this holiday season.
Visit the wineries of the Pleasant Valley Wine Trail to drop off canned food donations during our annual Cans for Cabs Food Drive.
As a "thank you" for your donations, you'll enjoy a special discount, tasting, or other "perk" on the day of your visit.
We appreciate your continued generosity and support. Thank you!
Holiday Toy Drive - December 1-13, 2026
The Pleasant Valley Wine Trail invites you to help us spread a little extra holiday cheer!
December 1–13, bring a new, unwrapped toy to any participating Pleasant Valley Wine Trail winery and help make the holidays brighter for local children and families.
✨ Small Gift. Big Impact. ✨
Enjoy a little wine country hospitality and a treat or perk, while giving back to our community. Thank you.
Under the Estrella Sky Winemakers' Dinner - Saturday, August 14, 2027 5-9PM
Join the wineries of the Pleasant Valley Wine Trail for an unforgettable evening at Hartley Farms in beautiful San Miguel wine country.
After a pre-dinner wine stroll with passed appetizers, enjoy the stars of the Estrella sky as you indulge in a delectable 4-course dinner menu, expertly paired with a selection of our wines. This evening promises an intimate and exclusive experience with our winemakers, as they pour their wines and regale you with their stories.
Live Music. Silent and live auctions.
