Annual Trail Events
We participate in the following annual trail-wide events. Many of our wineries also host additional events throughout the year. (Please visit the websites of our member wineries for additional event listings.)
Wine & Cherries Weekend – February 17 & 18, 2024
Join the participating wineries of our Trail for a “Wine & Cherries Weekend” to celebrate Presidents Day Weekend! Be sure to “Like” our Facebook page for updates leading up to the event.
Spring Oyster Crawl – Saturday & Sunday, April 27 & 28, 2024
Join participating wineries of our Trail for a weekend of wine & oysters. Be sure to “Like” our Facebook page for updates.
Pour Your Heart Out – Saturday & Sunday, July 13 & 14, 2024
Join participating wineries of our Trail for our newest event. Participating wineries will each donate a portion of sales to a local charity. Visit the Event Page to learn more and be sure to “Like” our Facebook page for updates.
Fall Oyster Crawl – Saturday & Sunday, Nov. 9 & 10, 2024
Join participating wineries of our Trail for a weekend of wine & oysters. Be sure to “Like” our Facebook page for updates.
Holiday Sip & Shop – Saturday, Dec. 14, 2024
Join the participating wineries of our Trail for holiday refreshments and wine/gift specials. Visit the Event Page and be sure to “Like” our Facebook page for updates leading up to the event.
Wine Festivals
Many of our trail wineries participate in wine festivals around the Commonwealth and beyond. For the most up-to-date list of where we’ll be, please visit our Facebook page or the individual winery websites.
Tours & Tastings
Sample award-winning varietals, learn pairing tips, or enjoy tours of winemaking facilities. Pack a picnic and bring your friends. We suggest making reservations for groups of 6 or more. Check our our limited-edition Tasting Pass to save on tasting fees.
Days and times vary by winery. View their schedules.