Historic Trolley Tours of Naperville

Ready to see Naperville from a whole new perspective? Historic Trolley Tours of Naperville offer a delightful one-hour journey that blends the city’s rich past with its vibrant present, perfect for locals and visitors alike who want to discover hidden stories and favorite landmarks.

Whether you’re a longtime resident or planning your first trip downtown, this guided adventure departs from the trolley stop at the SE corner of Jackson Avenue and Eagle Street and promises fun facts, great stories, and even a lighthearted group quiz at the end.

Why Historic Trolley Tours of Naperville Rank Among the Best Things to Do in Naperville

Tuesdays just got more exciting. From July 21 through August 25, 2026, the beloved “Trolley Chick” Annette Wehrli leads public Historic Trolley Tours of Naperville every Tuesday at 11:00 a.m. for $25 per person, all ages welcome.

This isn’t your average sightseeing ride—it’s a rolling history lesson that connects you to the heart of downtown Naperville, the Riverwalk, Naper Settlement, and the Century Walk while sharing tales of how the city grew from a small prairie settlement into the thriving community it is today.

What to Expect on the One-Hour Tour

You’ll board a fully enclosed, climate-controlled trolley right in the heart of downtown. Annette narrates the entire trip with enthusiasm, pointing out historic buildings, notable sites, and fun local anecdotes that bring Naperville’s story to life.

Expect a relaxed pace with plenty of opportunities to ask questions. The tour wraps up with a friendly group quiz—don’t worry, Annette is there to help every participant.

• Departs promptly at 11:00 a.m. from the Jackson Ave & Eagle St stop
• One hour of nonstop narration and sights
• All ages and comfortable for families or groups

Highlights Along the Route

As you roll through downtown Naperville and surrounding neighborhoods, you’ll catch glimpses of iconic spots that define the community.

• Historic architecture and stories tied to Naper Settlement
• Views of the scenic Riverwalk and Centennial Beach area
• Landmarks featured in the Century Walk public art collection
• Insights into DuPage County’s growth and Naperville’s unique character

Plan Your Visit

Tickets are $25 per person and available online at napervilletrolley.com/book-public-tours. Arrive at least 10 minutes early at the SE corner of Jackson Avenue and Eagle Street—tours depart on time.

The trolley runs rain or shine with heat and air conditioning. No coolers or food allowed, but sealed beverages with lids are welcome. Street parking is available nearby in downtown Naperville, and the area is walkable from many hotels and the Metra station.

• Great for families, couples, or solo explorers
• Combine with a stroll along the Riverwalk before or after
• Book ahead as space is limited on these popular Tuesday tours

Whether you’re looking to learn more about your own backyard or show out-of-town guests the best of Naperville, these Historic Trolley Tours deliver an authentic, memorable experience. Grab your tickets today and get ready to ding-ding your way through history!

Event Details At-A-Glance

• When: Tuesday, July 21 – Tuesday, August 25, 2026
• Where: Trolley Stop (Jackson Ave & Eagle St)
• Address: SE corner of Jackson Avenue and Eagle Street, Naperville, IL 60540, United States
• Admission: $25
• Organizer: Annette Wehrli
• Tickets / info: Get details

Dates, times, and pricing can change. Confirm the latest details on the official event page before making plans.

Looking for more? Explore other things to do in Naperville or browse the full Naperville events calendar.