Special Events
Celebrate in Iconic Style!
The Morgan Hill Wine Trolley hosts a variety of special public tours and events throughout the year. Whether it’s Halloween Lights tours, Farm Tours, Holiday Lights, or 21+ themed rides through South County wine country, a fun time is guaranteed!
Upcoming Events
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.
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.
Morgan Hill History Trolley Tour (Sept 12)
Step aboard the climate-controlled El Toro Trolley for a 70-minute journey through the full story of Morgan Hill. Departing from and returning to the historic Hiram Morgan Hill House, you'll roll past major landmarks in town. A docent from the Morgan Hill Historical Society will be on board to trace more than 10,000 years of history, from the indigenous peoples who first called this valley home, through the Spanish and Mexican Rancho eras, to the city we're celebrating on its 120th birthday. No stops, just stories, scenery, and a comfortable seat. Fully ADA accessible. Proceeds will be donated to the Morgan Hill Historical Society.
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.
Practical Magic: Cider, Wishes & Sisterhood (October 23)
🌝 Moonlit Margaritas & Wishes On the Trolley 🚎 Gather your soul sisters for a spellbinding evening aboard the Morgan Hill Wine Trolley. We’ll start with a “Midnight Margarita” at Willard Hicks before whisking you away to TenFiveOne Cider Co. for a specialty cider cocktail and a make-your-own wish jar activity. Dress in your witchiest attire inspired by the new 2026 Practical Magic 2 movie and the classic 1998 Practical Magic movie—black lace, velvet, and moonlit sparkle encouraged—for a night of cider, sisterhood, and just a pinch of magic. 🧙 Costumes encouraged, there will be a contest! 📆 One night only on Friday, October 23rd. Limited spots. Book now—this one’s going to be magical!
2026 Halloween Haunt Trolley Tour
The Haunted Vines Halloween Wine Tour (October 31)
Vino y Recuerdos: A Dia De Los Muertos Wine Tour (November 1)
One Day Only -- November 1st 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.
