On July 26, 2016, my mom, my daughter and I made the drive to Chincoteague Island on Virginia’s Eastern Shore. This was a trip we had always wanted to do, but for whatever reason the timing was never right.  I noticed an advertisement for the swim on Facebook, and booked a hotel that day (a couple months prior).

We ended up staying at the Fairfield Inn & Suites at Chincoteague on Main Street, which was right in the middle of everything, and had an awesome view of a bay of the Atlantic ocean.  All of this has to be pretty crazy for the residents, because their normal population of 3k swells to 30k! All the hotels in that area require a 3-night stay during the Pony Swim week, and their rates jump.

We arrived late on Tuesday and had to search out a place to eat – just an FYI: nothing is open after 9pm on Chincoteague Island! We ended up getting some pizza delivered from Famous Pizza and it was pretty good! Luckily the hotel had some frozen macaroni in the lobby, so HM was able to eat while we waited for the pizza to arrive.

Wednesday morning was the pony swim, so we got up pretty early and tried to head out to the swim spot.  The hotel provided hot breakfast, and we ate there every morning (hard boiled eggs, bacon/sausage, biscuits & gravy, waffles, etc).  They also provided bagged breakfasts and lunches at no cost which was so nice!

As soon as we left the hotel on Wednesday, the mosquitos started to eat us alive.  We had to find some spray, so we wandered a few blocks to the grocery store and picked up some Deet.  Lifesaver!  The mosquitos on Chincoteague Island are HORRENDOUS.  I don’t know how the residents do it!  Even with Deet we were ALL eaten alive during our trip!

Bug spray in hand, we waited for the bus to to the pony swim, but they were filling up before our stop and wouldn’t even stop for us (we were one of the last stops before the swim area). We ended up grabbing the jogging stroller from the car and walking to the swim, which was about 1.5 miles.  We arrived with plenty of time, but there were SO MANY PEOPLE that we literally could not see anything.  After standing in the ridiculously hot, blazing sun for about 45 minutes, we ditched our spot and decided to go find some shade along the road where they parade the ponies past after the swim.

We found a nice, shady spot outside of an artist’s studio, and everyone there seemed to have the same feelings about trying to find a spot by the swim! Everyone was super nice and the lady at the studio played bag pipes for us while we waited!  We also grabbed some subs from J&B Subs down the street.  A cold Coke was PERFECT.  IT WAS SO HOT.

The ponies eventually arrived and we got to watch the “Salt Water Cowboys” parade them down the street toward the fairgrounds.  At this point, we were hot, sweaty and HM ready for her nap, so we went back to the hotel for a bit.

After naps and showers, we went back to the fairgrounds to try and get a look at the ponies.  They are in fenced-in areas behind the fairgrounds, so you can look at the foals before the auction on Thursday.  I thought that was really neat and I would definitely recommend going to see them if you make the trek.

That night we attempted to get some seafood at The Crab Shack which was not a good experience with an antsy 18-month-old.  We ended up taking to-go and eating in the lobby of our hotel.

Thursday morning we woke up early and went to the pony auction.  There were so many people and no where to sit, so my mom ended up finding a spot in a shady area and HM and I wandered around in the shade for a bit.  My mom bid on a couple of ponies we liked, but they went up to $8k (yikes!) so we agreed it was fun to bid but probably not something we wanted to take on at this point 🙂

Thursday afternoon we hung out at the hotel, napped, sat by the pool, and had some cool showers (by choice!).  I had my mom pick up some tacos from “Right Up Your Alley” which were DELICIOUS!  It is a truck down an alley in Chincoteague and that was seriously the best meal we had the entire trip.

Thursday night we ended up getting seafood at “Steamers” which was perfect.  My mom and I split a seafood pot and HM had macaroni.  She enjoyed playing with the oyster shells once we had eaten them!  The restaurant was nice and loud, so she could make all kinds of noise and we could eat.

Friday morning we got up early again and drove a car out to the pony swim area.  Friday morning is when they swim the ponies back across from Chincoteague to Assateague, so we decided to try and see if we could get a spot to watch since we didn’t see anything from the first day.  There were quite a bit of people, but not nearly as many as the first day.  I was able to catch a few photos while mom chased HM around the parking lot 😉 I would definitely recommend going to Friday’s swim instead of Wednesday!  Especially if you have a young child or older adult.  It is just so hot.

Afterwards we decided to drive out to Assateague Island to see the beach area.  On the way, we passed the Chincoteague Pony Center where they were doing pony rides!  So we had to stop and HM LOVED riding a Chincoteague pony around a pen.  We stopped at Smokey’s and grabbed some barbecue, but the flies were terrible so we ended up eating in the car in the parking lot.  It was pretty good though!

Drove for about 15 minutes and arrived at Assateague Island.  We had to pay an entry fee (I don’t remember off the top of my head how much it was) and there was a bit of a drive from the gate to the beach.  The beach is really nice and you can see the wildlife area.  Apparently the ponies wander out to the beach sometimes to try and grab a snack from beachgoers!  We took a few pictures and hit the road back to Northern Virginia.

All-in-all it was a great trip, but VERY HOT. If I were to do it again, I probably wouldn’t take a small child, I would probably wait until they’re about 9.  It is just so hot and there is a lot of walking and watching, not as much hands-on.  So the kids would have to be ok with just standing in the heat for long periods of time. I would also make sure and take lots of bug spray/long-sleeved, breathable clothes and big hats/sun protection.  But I would definitely recommend going at least once!