10 Events That Are Even Better with a Trolley Ride

There's something inherently charming about a trolley ride. It turns standard point-A-to-point-B transportation into a memorable, photogenic part of the event itself.

Large open windows, classic wooden seating, and a distinctly vintage aesthetic — a trolley elevates the mood before you even arrive at the destination.

If you're looking to upgrade your next gathering, here are 10 events that are significantly enhanced by renting a trolley.

1. Weddings

Trolleys are a classic, beloved choice for wedding parties. The open, airy feel makes for incredible natural-light photos, and the spacious interior comfortably accommodates voluminous wedding gowns without wrinkling.

There's also a practical side: a trolley can shuttle the entire bridal party between the ceremony, photo locations, and reception without anyone getting separated.

2. Corporate Retreats

Break the ice before the retreat even begins. A trolley ride from the office to the venue sets a fun, relaxed tone — encouraging team members to step out of their corporate shells, mingle, and start conversations they wouldn't have at their desks.

It's team building that starts the moment everyone boards.

3. Family Reunions

Keep the whole extended family together. A trolley is perfect for touring the city, visiting childhood homes, or keeping everyone on schedule as you head to a massive group dinner.

Bonus: the kids absolutely love it.

4. Bachelorette & Bachelor Parties

Safe, fun, and capable of holding the entire crew. A trolley serves as the perfect moving basecamp for a night out on the town or a daytime winery tour.

No one has to be the designated driver. Everyone stays together. And the trolley itself becomes a highlight of the photos.

5. Historic City Tours

If you're hosting a group in a city with rich architecture and deep history, the large panoramic windows of a trolley provide the absolute best views for sightseeing.

A trolley doesn't just transport you through a city — it makes you feel like a part of the city's living history.

Pair it with a local guide and you've got a private, curated tour experience that beats any bus tour.

6. Festival Transportation

Avoid the nightmare of festival parking and rideshare surges. A trolley shuttle can drop your group right at the entrance, keeping the excitement high and the logistics invisible.

No circling for parking. No $80 Uber surge. Just smooth arrival and departure while everyone else is stuck in traffic.

7. Holiday Light Tours

Rent a trolley in December, bring some hot cocoa and blankets, and take a magical, curated tour of the best holiday light displays in town.

It's a fantastic tradition for friends and families — and one of the most popular trolley rentals of the year. Book early, because December dates go fast.

8. Prom Transportation

A unique, spacious alternative to the traditional limousine. A trolley allows the whole friend group to travel together, take great photos, and actually stand up and move around comfortably.

Parents love it because it's safe and supervised. Kids love it because it's genuinely fun and different.

9. Tailgating & Sporting Events

Rally the fans. A trolley can transport your group straight to the stadium, letting everyone enjoy the pre-game excitement safely and without the headache of stadium parking fees.

Decorate it in your team's colors. Blast the fight song. Make the ride to the game part of the experience.

10. Milestone Birthdays

Celebrate a 30th, 40th, or 50th birthday in style. Hop from your favorite restaurant to a cocktail bar, and finally to the main venue — all in a private, festive trolley.

It turns a night out into an event. And the birthday guest of honor gets a ride they'll never forget.

With ARE+, booking unique transportation like a trolley is simple, professional, and completely customizable to your event's specific needs. Tell us the occasion, the headcount, and the vibe you're going for — we'll handle everything else.