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My Chincoteague Island History Tour aboard the Pony Express Trolley

Posted: March 16th, 2017

“With my high starched-collar and my high-topped shoes
And my hair piled high upon my head
I went to lose a jolly hour on the trolley
And lost my heart instead”
Lyrics from “The Trolley Song” * sung by Judy Garland, written by Hugh Martin & Ralph Blane

I just can’t talk about the Trolley without that song playing in the background of my mind and the song just fits. Trolleys must be one of the most delightful modes of transportation ever invented and I’m so glad that we have them right here on Chincoteague Island! You can catch a Trolley many times during the Summer. It’s a great way to get around the Island. But did you know that there are also Narrated Chincoteague History Tours on the Trolley as well?

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Passengers waiting to board the Trolley for the Chincoteague History Tour

The Narrated Chincoteague Island History Tour on the ‘Pony Express’ Trolley

While riding a trolley, guests of the History Tour view scenic Chincoteague sites while listening to a tour guide provide a very interesting history of the Island. You can sit back, relax and be led through a trip back in time by a knowledgeable volunteer guide.

Getting a ticket for the Island History Tour aboard the ‘Pony Express’ Trolley

The first thing you should do when planning your tour is to view the Pony Express Trolley Brochure . The brochure will tell you the days and times that the tour is scheduled. It will also list the cost, which is based on the guest’s age. At the time of my tour, the cost was $4 per adult, $2 per child 12 and under, and free for children 2 and under on laps.

You cannot buy your tickets over the phone. You must buy them the day of the tour. The trolley departs from The Chincoteague Center, located at 6155 Community Drive.

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The Chincoteague Center

I was a little worried that I might not get a place on the tour, so I arrived right at 1:30 which is the earliest you can purchase your ticket. Right in front of the building there is an awning structure at the main entrance. I had no trouble finding the ticket sales area. There was a volunteer sitting at a table next to a clearly marked sign for the ‘Chincoteague Island History Trolley Tour’.

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Tour Ticket Sales area at Main Entrance of The Chincoteague Center

Thankfully, I was one of the first people who purchased their ticket. I didn’t see them turn anyone away. But by the time our tour started at 2pm, a few last minute guests arrived and the bus had become full. Usually, there are two tours available, so even if you cannot take the 2pm tour, you can buy a ticket for the next tour which is at 3:15pm.

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Inside the Lobby of the Chincoteague Center

Hopefully, you will have a few minutes before your tour departs. The Chincoteague Center main entrance is open and they have restroom facilities. There is no bathroom on the trolley.  The awning provides great shade, but if the weather isn’t comfortable, you may wait in the main lobby area of The Chincoteague Center.

All Aboard

All Aboard

The Tour

The tour was about an hour in length. The pleasant trolley driver told me that I hit the jackpot and had Louisa as my tour guide. The driver was right, Louisa’s knowledge of the history of Chincoteague Island coupled with her amazing storytelling skill made the tour phenomenal. I could feel her passion for the island and it’s unique heritage as she would point out a building or landmark and described the event that had taken place long ago.

Louisa, the Tour Guide

Louisa, the Tour Guide

What do you learn on the History Tour?

I don’t want to give away any specifics, but you can learn how this tiny island inspired a best selling novel, supported a person who worked his way into the ‘Guinness Book of World Records’, and became home to a shipwrecked Spanish boy when Islanders took him in as their own. I’ve always liked how a good song and or good story, can touch your soul and make you love it. The History Tour felt like a date with the Island. It made me remember the treasure that is this little Island.  A good tour guide can make all of the difference. Did I mention that the tour guides are volunteers? That’s true love of an Island.

Where Does the Trolley Go?

The history tour takes the route of the ‘Pony Express’ Trolley stops. You can look at a map of the route here.

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Interior of the Trolley

What kind of weather is best for the Chincoteague History Tour on the Trolley?

When I went, it was a beautiful day in late August and the weather was sunny and still warm, but the trolley was comfortable and was air-conditioned. However, I think the Chincoteague History Trolley Tour would be equally as enjoyable on a rainy day. Whatever the weather, you stay inside the trolley the entire tour, so it really can be done in any kind of weather. Just choose the day that works best for you.

How Long Does it Last?

The tour lasts about an hour.

Is the Trolley Handicap Accessible?

Yes, there is an electric ramp on the trolley for Mobility Scooters or Power Chairs to board the trolley, as well as a designated spot for the scooter or special needs chair. I think it would be wise to arrive a little early so you can be boarded prior to the trolley being filled with other people.

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Should I take my young child?

It depends, here’s some information to help you decide. The tour is about an hour long and the trolley does not have a bathroom. Also, the trolley never stops to disembark for a break. There is no eating or drinking allowed on the trolley. School aged children might tolerate and even enjoy the tour. For those with preschool or toddler aged children who still would like to experience the trolley, I would recommend simply taking a ride on the ‘Pony Express Trolley’.  The ‘Pony Express’ Trolleys operate daily during the summer and use the exact same trolleys that are used on the history tour. Here is their schedule. Just grab some quarters and take the trolley ride on your own tour around the island! My little ones love doing an impromptu “tour” on the trolley. It’s an inexpensive and cooling ride on a hot summer day. We often get off at Memorial Park for the playground or skate park where there is usually a nice breeze from the water. Other days,  we’ll stop at one of the Ice Cream Parlors on Maddox Boulevard. Ask the business for a free trolley token during your checkout and it won’t cost you for your next leg of the trip.

What Should I Bring with Me?

Definitely bring your camera or camera phone and your payment for the tour. Parking is free and abundant around the Chincoteague Center. Please do not bring food, drink, cigarettes or pets.

What Months of the Year do the Tours Operate?

The Pony Express Trolley operates seasonally, with tours every Tuesday and Thursday starting in early July and ending in early September.

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Would I recommend taking the Chincoteague Island History Trolley Tour?

My answer is a resounding yes! Unfortunately, I didn’t see a Judy Garland look-a-like and none of the other passengers spontaneously erupted into song and dance. But I did fall in love with an Island all over again while on the Chincoteague History Tour aboard the ‘Pony Express’ Trolley. The Island and the Trolley are perfect for each other, in a word they are both charming.

Even better, there are so many things to experience here that are just as magical. For more information on the Narrated Chincoteague History Trolley Tour, the Pony Express Map & Schedule, and many other Activities, please visit our website www.chincoteague.com . Whether it’s your first visit or you’re a returning guest, our site is there to help you plan a trip that you can fall in love with.

~Happy Trails!


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