Special Events

✨ All the Swiftie eras, one night on the trolley

Taylor and Travis are saying "I do" — and we're celebrating in full Swiftie fashion. Board the trolley dressed as your favorite Taylor era (Fearless, Red, Reputation, Bejeweled — all welcome) for a cocktail at Willard Hicks, then sing your heart out to Taylor bangers all the way to Tuscan House Vineyards for wine, live DJ and charcuterie.

Gentlemen, this one's for you too. Come repping Travis in his Chiefs gear, a Taylor-approved friendship bracelet stack, or one of his own iconic looks — because every great love story has a leading man. Kelce-coded outfits are strongly encouraged.

Come ready to raise a glass to the greatest love story of our era. Friendship bracelets, cowboy boots, and sequins all welcome. Outfits optional, but best dressed wins bragging rights (and maybe a fun gift.)

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.

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.

🎶 The Only Rolling Karaoke in South County - now for kids! 🎤

Looking for a fun family outing that’s anything but ordinary?

Family Karaoke Trolley is a one-of-a-kind sing-along adventure where the fun happens on board.

Hop aboard our luxe El Toro Trolley for a 90-minute rolling karaoke party through South Santa Clara County on select Thursday afternoons this summer. Sing your favorite songs, enjoy the ride, and make memories together as we cruise through Morgan Hill and scenic backroads with music, laughter, and a microphone always ready. Whether you’re belting out Disney classics, pop hits, or family favorites, everyone is invited to take the spotlight.

🚃 Pick-up and drop-off are at the Train Depot in downtown Morgan Hill. [17300 Depot Street, Morgan Hill, CA 95037]
🌲 Our midway stop is at Christmas Hill Park for a stretch and a restroom break.

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.

🎶 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.