“This is the worst vacation. Ever.” The young boy in front of us at the Pony Swim was obviously not as excited as his sisters to see real live ponies. He wasn’t alone. Based on my own brother’s grumbling and moodiness, it was abundantly clear that watching ponies was not his idea of a great vacation either. Not even if they were wild ponies. Especially not if they were written about in some girly-children’s book. Luckily for all those unfortunate family members who have no interest in feral horses, but find themselves along for the ride on a family vacation, there’s plenty to do in Chincoteague that doesn’t involve pony viewing.

Explore the Length of the Downtown

Chincoteague’s small downtown doesn’t take long to walk. Between Miss Molly’s Inn at one end and the Carnival Grounds at the other end can be found a couple restaurants, souvenir shops selling pony and seaside themed trinkets (ok, you can’t completely get away from Ponies in Chincoteague), a small movie theater, and my personal favorites, the library and bookstore. Do stop by Sugarbakers for one of their AMAZINGLY gooey cinnamon rolls, but after that continue on past the statue of Misty to the two literary haunts of the downtown.

Misty of Chincoteague Statue
Misty of Chincoteague Statue

Sundial Books

Sundial Books is the kind of place where the owner will remember you, even if you’re just passing through town. If you’ve been following this blog, you might have discovered I’m kind of a Harry Potter fan. Like the kind that will stay up until midnight to attend the release party at the nearest bookstore. Or I meant to anyway! The day before I eagerly questioned the man behind the desk at Sundial Books about that night’s party for the release of Harry Potter and the Cursed Child. I wasn’t planning to miss the last midnight release party for a Harry Potter book. Oops. Slept right through it. But I was first in line the next morning when the shop opened! As I pushed open the door, the man looked at me, picked up a copy of the book and held it out. “I fell asleep…” I admitted sadly. “I noticed.” was all he said as he slid it across the counter towards me.

Chincoteague Sundail Books
Even Sundial Books in small Chincoteague, VA had a midnight Harry Potter party!

Sundial Books has a little bit of everything to suit everybody’s interests and besides books, the place itself is so much fun to explore. The rooms just keep going! You could spend hours there prowling the shelves of the various genres which can be found on bookcases hidden in hallways, back rooms, upstairs… At times our party got separated and it took a surprising amount of searching to find each of our companions sitting before various shelves absorbed in a find.

Chincoteague Sundail Books
Just two of the various rooms of Sundial Books

The Library

Chincoteague’s independent Island Library is made up of two buildings. The front, boxy looking building, is one of the oldest buildings in town. Prior to becoming the library it sat as an abandoned barber shop. After some renovations and relocation to its current position, it opened as Chincoteague’s very small library.

Chincoteague Library
Chincoteague Library

More recently, thanks to donations and grants, the library was able to add an addition. This octagonal shaped addition is inviting, with warm colors, and natural light through large windows. There are plenty of study spaces tucked between bookshelves upstairs while downstairs you’ll find a circle of cozy chairs. They do offer Wi-fi, so it’s the perfect location to get some work done while on vacation.

Chincoteague Library Interior
Chincoteague Library Interior

Experience The Maddox

If strolling in a cute seaside town isn’t quite your ideal, how about driving along a street with a busy beach side boardwalk feel? Then you’ll want to spend time on Maddox Boulevard, fondly known as The Maddox. If you don’t have a car, you can easily get between the downtown and the Maddox by walking or hopping on the trolley. Several businesses in the downtown provide tokens for the trolley.

Maddox Boulevard is the street where you’ll find food trucks, ice cream parlors, mini golf, beach supply shops, hotels, and bike & motorized vehicle rentals. To find the beach you’ll have to drive through the nature reserve to the other side of Assateague Island, but this street ends in the bridge to the island, so it’s at least on the way to the beach.

Chincoteague Mini Golf
Chincoteague Mini Golf

The best time to play Mini Golf in Chincoteague is in the evening around sunset. The temperature cools down and the mosquitoes never seem to bother us. As wait times at restaurants during Pony Penning Week can be up to an hour, I recommend putting yourself on a wait list at one of the eateries and then going to play a couple rounds of mini golf across the street while you wait.

We did exactly this, but on this particular night a huge storm rolled into town. The wind began to pick up while we played, but compared to the hot muggy weather we’d had so far, it felt really good. Fortunately, the rain held off while we golfed. It wasn’t until we’d been seated at the restaurant that the sky opened up. We ate a large platter of fried seafood as thunder shook, lightening lit the sky, and the lights flickered a couple times. After dinner we found ourselves standing in a warm deluge of rain waiting for the trolley back to the Inn as thunder and lightning continued around us. We were soaked by the time the trolley arrived. There was no need to take a shower to remove all the sunscreen and bug dope from the afternoon any more. As had happened so often in the last couple weeks of vacation, we were assured, this time by the driver, that this weather was totally unusual. There seemed to be a lot of that going around.

Shop Local

When I travel I prefer shopping for locally crafted souvenirs rather than the made-in-China kitsch found in many of the shops. In Chincoteague, this means leaving the Downtown and Maddox roads for residential neighborhoods.

Residential Yard Stands

One of my favorite things about Chincoteague’s residential streets is that not only are several of the houses decorated with numerous whelk shells, but you can often find booths set up on people’s yards selling whelk shells on the honor system. Put the suggested amount of bills in the coffee can, and pick out some shells. Depending on how crafty the seller is the shells may have hand-painted designs or might have been turned into plant pots.

Chincoteague Whelks
Whelk shells & potted plants

Saturday Farmers Market

Chincoteague also has a Saturday Farmers market where local crafters, artisans, farmers, and photographers sell their small stock. (Things you wouldn’t want to sell on your lawn by the honor system.)

Unfortunately, not having a kitchen during our stay, we could not take back any of the fresh produce being sold. I therefore spent my time browsing the arts and crafts. Unsurprisingly, I found painted horseshoes. If you’re going to get a horseshoe to hang above your door, Chincoteague seems like the place to do it. These horseshoes have been used by actual Chincoteague ponies. (I didn’t get one because I wasn’t thrilled with the painted design, but Micah also wasn’t thrilled with the idea of putting a horseshoe above our door at home, “We’re an Alaskan household, not a cowboy household.” I’m just thankful he hasn’t put a pair of antlers above our door!)

Photographers sold their newest shots of this year’s pony swim day. I found a beautiful image of a pony and foal together at the water’s edge. It was so simple and yet so powerful. Just a mother and foal spending a few moments together before being separated the next day at the auction.

There was also a woman selling what promised to be both bug dope and anti-itch after bite spray, and I’m pretty sure she said it would also cure anything and everything else in between.  My mosquito bites had swollen to about 3-inches around and nothing made them shop itching so I was willing to give it a try. Anything to make them stop itching!

Sample the Numerous Food Options

For a small town, Chincoteague has several different food options.


If you’re looking for a nice sit-down dinner downtown, I’d recommend Bill’s. We ate here twice in one week. The portion sizes are enough to share, or get two dinners out of.

Sugarbakers Bakery & Cafe
The downtown bakery has the most mouth-watering display of doughnuts, scones, and gooey buns I’ve seen anywhere. Although our B&B offered breakfast, first breakfast was soon forgotten upon walking into the bakery. You’ll definitely be walking out with more than a coffee.

The Maddox

Island Creamery & Mr. Whippy
The first eatery you’ll notice along The Maddox is the Island Creamery because there is ALWAYS a line out the door and down the block. This is because the creamery makes 30 hand-made flavors at a time and 1 scoop is SO large that it comes with a spoon! Poor Mr. Whippy next door serves soft serve, which is also delicious, but it is never as impressively busy.

Chincoteague Island Creamery
Micah’s 1 scoop of Blueberry at the Island Creamery

Taco Cart & Sea Star Café
If you’re looking for some to-go options, I’d recommend either the Taco Cart or sandwiches from Sea Star Café. These both came both highly recommended, and did not disappoint. Both are great options for grabbing a meal to go on your way to the beach or before a sunset boat cruise.


For those inclined to get off the streets and out into nature, check back next week to find out what Assateague Island offers besides Chincoteague Ponies.

Let’s Talk

Have you ever been dragged on a trip you didn’t want to go on and then had fun anyway? Tell me about it in the comments below!


  1. I am like your brother not a pony enthusiast. On the other hand I like to see a pony or a horse as it gives me a happy feeling to remind me that in the morning go to work or go shopping I can get into my car or bicycle and I do not have to get on my horse or go in my horse driven carriage. That feeling is especially great on a rainy or snowy day. On those days I can go wherever I want and not getting wet and when I park my car and get out I can open my umbrella and do not have to fool around to tie the horse somewhere and think about the poor horse getting soaking wet while I am in the nice and warm office or in the shopping center.

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