Do I need to bring my own pickleball gear?

No, equipment is provided; just wear comfortable clothes and be ready to play.

Is this suitable for beginners?

Absolutely, the lesson caters to all skill levels, from complete novices to experienced players.

How many stops are there?

The tour has multiple stops, including a brewery, gameplay sessions, and the golf simulator at Beyond Golf.

Is the tour wheelchair accessible?

Yes, the trolley and venues are accessible, but please notify us in advance.

What if the weather is bad?

Tours are scheduled with contingency plans; contact us for weather-related updates.

Can I participate solo?

Yes, solo participants are welcome and will join group activities.

Outdoor Recreation & Sports Experience at SMASH*SIP*RIDE in Omaha

The Pickleball Trolley Tour in Omaha offers a dynamic outdoor activity that combines sports, socializing, and local flavor in a lively, urban setting. Located in the heart of Omaha, this experience is perfect for those looking to enjoy active leisure while immersing themselves in the city’s vibrant craft beverage scene. The tour begins at Lucky Bucket Brewery, where participants sip on craft brews and get introduced to the fast-paced game of pickleball. From there, the trolley whisks players around the city, making stops for instruction, gameplay, and social interaction. The highlight is the professional pickleball lesson, where players of all skill levels can learn techniques, then put their new skills to the test in fun, friendly matches. Afterward, the tour transitions into a laid-back phase at Beyond Golf, where guests indulge in gourmet food, test their putting skills, and unwind with good company. What makes SMASHSIPRIDE in Omaha stand out is its clever combination of urban adventure, sports, and local craft culture, all within a convenient and accessible city setting. This trip offers a unique chance to elevate your outdoor activity repertoire in a lively, social environment. Perfect for groups or solo adventurers, it blends active engagement with laid-back social scenes, making it a popular choice for locals and visitors alike. Whether you're new to pickleball or a seasoned player, the mix of fun, instruction, and city vibe makes this tour a memorable outing.

About Ollie the Trolley

Ollie the Trolley operates guided trolley experiences in Omaha, Nebraska. The company offers seasonal and specialty tours that combine local history, neighborhood lights, and recreational activities. Signature experiences include the Pickleball Trolley Tour — with two drinks, two trolley rides, and a professional pickleball lesson at Midwest Pickleball Club — as well as Halloween Lights Tours guided by the Omaha Halloween Yard Haunts group. Holiday Lights Tours run from the weekend after Thanksgiving and showcase displays installed by Brite Ideas. Haunted Cemetery Tours run every Sunday from September 21 to November 9 and feature newly trained Historians dressed as undertakers who present Omaha’s darker past, including stories about gangsters and historic brothels.

Tours depart from central Omaha locations and partner with local businesses such as Lucky Bucket Brewery and Beyond Golf for food, beverages, and activities. Each tour is structured as a two-hour experience except where noted, with curated routes, knowledgeable guides, and on-board narration. Ollie the Trolley focuses on accessible group outings that blend entertainment, education, and local commerce.

Customer safety and local collaboration are emphasized; tours work with community groups and contractors named in promotional materials. Booking information, schedules, and seasonal availability are published for each tour so guests can plan trips in advance. The business targets local residents, visitors to Omaha, and groups seeking themed outings that highlight the city’s attractions and neighborhood traditions. Reservations are available online or by phone, and tours accommodate private bookings, group rates, and seasonal scheduling for community events.