The Mystery of Chincoteague Island

Chincoteague Island at sunset

As an IT professional for more than 35 years, I’ve worked with and become friends with many colleagues who hail from different parts of the country as this is sometimes a consultant driven field. As consultants, they do a ton of traveling for both work and pleasure to places I’ve never heard of. But none of them have even heard of Chincoteague Island, yet here I am. It’s a little island on the coast of Virginia, just south of Maryland, nestled between the mainland and Assateague Island. It’s about as wide as Manhattan, but only half its length with less than 3,000 residents. It’s one of the few places where you can stand in the same spot and see the sunrise from one direction and the sunset from the other. We made the trip on a suggestion from my wife’s friend Georgia, who once owned a home on the island.

Quite frankly, we were so disappointed with our last trip to the Montauk Music Festival, we started looking for a new destination next year. The music festival, held before Memorial Day, was a way to draw people out east a weekend early. There were discounted hotel rooms and activities. Restaurants choosing to be open routinely partnered with hotels to offer discounted meals. Not anymore.

Back in 2017, I wrote about the Montauk Music Festival, revealing one of Long Island’s best-kept secrets, so maybe I had something to do with it. The greed of Montauk has taken over as hotels are no longer offering discounted rooms, instead, exploiting the added weekend with regular prices. Once they realized people would come out a week early, they found a way to take advantage of it. Georgia had always touted Chincoteague as Montauk 20 years ago, a simpler less refined Montauk. Now they might as well call it East-East Hampton since its priced people like us out of the market. Goodbye, Montauk. Hello Chincoteague Island! Of course, I run the risk of ruining this particular place also, but I’ll take my chances. Less than six-hours from Long Island (about 300 miles), Chincoteague is a seafood lover’s paradise. With only two main roads, you can eat at a different place every night for two weeks. Besides sit-down restaurants, there are smaller places that serve great food, like Pico Taquito. There’s a BYOC, where you can build your own cookie and many different ice cream places. You’ll find two miniature golf courses and virtually every store has a gift shop attached to it. It’s just a couple of miles from the beach on Assateague (right over the bridge), and there are campgrounds, small cabins, vacation homes and hotels galore. Want to know the best part? It’s not going to cost you a fortune.

At Montauk, it cost me $14 for one mixed drink. At the Chinco Tiki Bar, where we found some live music, we had food and drinks for less than $40. Dinner at AJ’s on the Creek, including a 16-oz strip steak and cocktails, set us back $66 for two people. Come on now!
I tell you all of this because I believe when you go on vacation, you shouldn’t have to break the bank to get what you want. Chincoteague Island is a throwback to what that used to be. We rented bikes and cruised around town, stopping to buy hokey T-shirts like every other tourist. But never once did we look at each other and say, “this is a rip-off,”—a common phrase this spring at Montauk. What’s that, honey? No, of course, I’m not writing a column about Chincoteague Island. I would never do that. I already ruined the Montauk Music Festival for us. Love ya, honey! On second thought, maybe Chincoteague Island isn’t for everyone. But if you do go, please don’t tell my wife how you found out about it.

Paul DiSclafani, a Massapequa resident, is a 2018 Press Club of Long Island award winning columnist and an Anton Media Group contributor since 2016.


  1. Paul, don’t take yourself so seriously… your 14 readers probably didn’t make Montauk Music Festival take off. It’s been rocking for years long before 2017. BTW it’s a wonderfilled experience still. Save up and come visit next year 🙂

    • BB – I never take myself seriously, ever. But I’ve been going to the Festival every year since it started and it went from virtually nothing to overdone. The relocation of the outdoor music to the lighthouse was a disaster. Now it cost you to get in (parking AND an admission fee), you can no longer walk from your hotel, and two bands are playing at the same time on different sides of an almost un-climbable hill side. The hotels are no longer offering deeply discounted rates. It’s become a money grab and lost it’s original appeal – a laid back weekend with free music everywhere you went. I’m sorry, but you can have it. What was once great has been ruined…

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