Special Events
Celebrate in Iconic Style!
Upcoming Events
A Totally Awesome Night on The Trolley (July 17)
The 90s called — they want you on this trolley! Dust off your scrunchies, lace up your platforms, and dig out your best decade look — because we're throwing it all the way back to the 90s. Board the trolley for a night of pure nostalgia, starting with a themed cocktail at Willard Hicks before we roll out to Cottage Creek Vineyard for wine and live music by the Crush Band. Come dressed for the decade and stay for the drinks — this is a night you won't forget (again). Whether you're serving full TLC, fresh off the Fresh Prince set, or just vibing in your best grunge flannel, all 90s looks are welcome. The music will be bumping, the wine will be flowing, and the only thing missing is your old mixtape. Limited seats. Don't want none unless you got tickets, hun.
Ritmo & Vino (August 14)
Latin Music Nights on the Wine Trolley Turn up the heat on a Friday night -- Latin style. From salsa to reggaeton, bachata to cumbia, the trolley is your dance floor and Morgan Hill wine country is your backdrop. Your night begins with a signature cocktail in Downtown Morgan Hill at Willard Hicks before climbing aboard our trolley for a stylish ride to and from J. Winston Winery. At the winery, sip wine, enjoy a personal charcuterie, and spend the evening dancing and singing along to the biggest Latin hits. Come ready to move, sip, and celebrate the best night of the week.
Mrs. Roper Romp on the Trolley (August 28)
Throw on your caftan, tease your hair, and join South County’s most fabulous trolley ride! Grab your besties and channel your inner Helen Roper for an evening of laughter, wine, and unforgettable fun. Inspired by the beloved Three’s Company character, this themed trolley experience celebrates bold prints, chunky jewelry, curly wigs, and the carefree spirit of everyone’s favorite landlady. Stanleys, Jacks, Krissy's or Janet's are always welcome too! We’ll kick off the evening in Downtown Morgan Hill with a welcome cocktail at Willard Hicks before boarding the trolley and heading to Besson Family Vineyards for a hosted glass of wine and Regal Beagle mini-sliders. Along the way, expect plenty of 70s and disco favorites, sing-alongs, dancing, and lots of photo opportunities. Whether you’re a longtime fan of Mrs. Roper or just love an excuse to dress outrageously with friends, this is a night out you won’t want to miss! Come ready to move, sip, and celebrate the best night of the week.
South County Farm Tour
A fresh air farm adventure through the backroads of South County Hop aboard our iconic open-air cable car for a wholesome ride through South County’s hidden gems. We’ll pick you up at the Morgan Hill Train Depot and head out for a relaxed day visiting local farms, meeting friendly animals, and enjoying a hands-on u-pick experience depending on the season. Fresh air, local flavor, and farm-to-fun memories await. Perfect for families, friends, or anyone looking to slow down and enjoy a day in the country.
Karaoke Trolley Nights (21+)
🎶 The Only Rolling Karaoke Party in South County 🎤 Looking for a night out that’s different from the usual bar scene? Karaoke Trolley Night is a 21+ karaoke experience where the party happens on board! Hop on our luxe El Toro Trolley for a 90-minute rolling karaoke party through South Santa Clara County. Sing your favorite songs, enjoy the ride, and let loose while we cruise scenic backroads with music, lights, and a microphone always ready. This tour is planned every other Thursday night. NOTE: This is a public event. To reserve the entire El Toro Trolley for a private karaoke event, reach out to us at cheers@mhwinetrolley.com.
Earth, Wind & Fire Wine Tasting Tour (September 20)
The 20th Day of September Get ready to groove—this ride brings the funk and the ultimate Earth, Wind & Fire playlist! Hop aboard our iconic cable car trolley and embark on a unique and unforgettable wine-tasting adventure through the rolling landscapes of the south Santa Clara County wine country. Our Earth, Wind & Fire Wine Tasting Tour starts and ends in charming downtown Morgan Hill and offers a delightful blend of scenic beauty, exceptional wines, and wine tasting at three charming wineries.
Vino y Recuerdos: A Dia De Los Muertos Wine Tour (November 1)
One Day Only -- November 1st (Sold Out!) Raise a glass to life, love, and those we remember. Step aboard the Morgan Hill Wine Trolley for a vibrant Dia De Los Muertos celebration on wheels. On November 1, we’ll sip our way through three local wineries, surrounded by lively music, colorful decor, and the warmth of honoring loved ones. Dress in your finest calavera face paint or festive florals and join us for a toast to life and memories — Latin pride and wine country charm in one unforgettable afternoon.