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The Ultimate Guide to Chincoteague Island VA

Sunset over the Chincoteague Channel

Chincoteague Island is a small-town beach community (only 7 miles long and 3 miles wide) that has that southern charm that makes it so special with so much to explore and do. Waking up to beautiful sunrises and ending your day with stunning sunsets, Chincoteague should be on your list of places to visit, at least once if not more, in your lifetime. Chincoteague has something for everyone from families with young children to retired folks, this community is one to be enjoyed.  

Chincoteague Islands Wild Ponies

Go see the Wild Ponies

In my opinion, this is the real reason everyone goes to Chincoteague, the wild ponies.  They are simply beautiful in their own environment and are truly a sight to see.  It’s a short ride from anywhere on the island to get to Assateague Island National Seashore where you can experience these fine animals.

The ponies are “owned” by the Chincoteague Volunteer Fire Department and they give them healthcare and food when needed.  They are allowed to live on Assateague Island by a special permit from the US Fish & Wildlife Service.

During the month of July, the “saltwater” cowboys (who are volunteer fire personnel) round up the ponies for the annual pony swim and auction.  This event began in 1925 after the forming of the Chincoteague Volunteer Fire Department, to raise money for firefighting equipment.  This was the outcome of two damaging fires that destroyed many acres on the opposite sides of the island.

During this event, you can see the ponies swim over the Assateague Channel to Chincoteague.  There is a parade of about 100 ponies, in the heart of town, making their way to the carnival grounds where they are rested until the auction the following morning(Friday) at 8 am.  This happens the last Wednesday before the last Thursday of July every year.  The unsold ponies are then returned to Assateague Island on Friday.  All monies from this event go to the fire department to supply firefighting services to the town.

This event draws about 40,000 spectators from around the world each year.

Assateague Island Lighthouse
Assateague Island Lighthouse

Visit Assateague Island National Seashore

Assateague Island National Seashore (on the Virginia side) offers the peacefulness and the beauty of what you’ve come to expect from our national park service. It’s a short car or bike ride to Assesstague Island National Seashore and you aren’t even charged the national park fee when you arrive by bicycle.

Not only can you see the wild ponies and other wildlife here there are numerous hiking and biking trails that are easy level paths enjoyed by everyone. You can climb the lighthouse, go to the beach and take a refuge bus tour. For detailed information of Thing to do on Assateague Island refer to this post, https://ourusaadventures.com/visit-assateague-island-virginia/.

Enjoy some Ice Cream

There are many choices in this small town to get your daily ice cream fix.  From homemade to soft serve to cookie ice cream sandwiches, ice cream is a big part of the history of this beach community. In addition to the fine ice cream they serve, all of these places serve fresh coffee all day. So when you need your coffee fix go to the local ice cream shop! The following places are all located on Maddox Blvd.

Island Creamery

A landmark since 1975, The Island Creamy is famous for its multiple flavors of homemade ice cream made fresh daily from locally purchased ingredients. Some of their flavors include bourbon caramel crunch, pony tracks, java jolt, cotton candy, and birthday cake. They also have special seasonal flavors like apple cider sorbet, peach, cannoli, and egg nog.

When you walk into Island Creamery you can smell the freshly baked waffle cones.  There also offer vegan ice cream (made with coconut milk) and sugar-free treats.  A trip to Island Creamery is a must do when visiting Chincoteague.

Mister Whippy

If you’re looking for soft serve ice cream, Mister Whippy’s is the place to go. Your choice of vanilla, chocolate or twist, this homemade soft serve is served in homemade waffle cones, sundaes, specialty sundaes, and milkshakes. 

Lil whippy is located inside Mister Whippy and serves a variety of homemade fresh donuts and cupcakes as well as bagels, cinnamon rolls, and muffins. All kinds of fresh hot and iced coffees and teas are available all day long.

BYOC Build Your Own Cookie

Build Your Own Cookie(BYOC) is a seasonal food truck that serves warm homemade cookies topped with ice cream and toppings. They offer 5 different kinds of cookies including cake batter sugar, chocolate chip, and fudgy brownie.  Add your favorite choice of 15 ice cream flavors and top it off with different toppings and candy and you are in for a treat.

Ride Chincoteague Island’s the Pony Express

The Town of Chincoteague provides a seasonal trolley system open to the public. The trolley has 24 stops throughout the island including many hotels, restaurants, campgrounds, shops, parks, and ice cream parlors.  This service costs only 25 cents and runs every day from 5 pm to 10:30 pm (extended hours available during festivals and special events). You can get tokens for a free ride from many of Chincoteague’s merchants displaying a Take-A-Token sticker.

From mid-June through Labor Day, on Tuesday and Thursday, local volunteers offer a one-hour historic trolley tour around Chincoteague Island. These scenic and informative tours begin at the community center.  Tickets can be purchased on the day of the tour beginning at 2:15 pm. Cost is $4 for adults and $2 for children under 12. Tours hours are 2:45 pm and 3:45 pm.

Eat at a Food Truck

On Maddox Blvd, there are numerous seasonal food trucks for everyone’s taste.  These trucks are open mid-April through early October depending on the weather. Woody’s Serious Food, Smoky’s BBQ, Backyard Firepit, Bettye’s Burgers, Lily’s Little Mexico, Bayside Burrito and Pico Taqueria offer snacks to full meals and most places have outside seating for your convenience.

Sandy Pony Donuts makes all flavors of homemade donuts and a great place to get coffee.  They also have homemade teas.  Build Your Own Cookie serves homemade warm cookies with ice cream.  Both are a great treat after a day on the beach.

There is also a taco truck, Right Up Your Alley, located at 2295 Main Street. All these food trucks get rave reviews on Google and TripAdvisor. Unfortunately, none of the trucks were open when we were in town.

Go Shopping

As one would expect from a beach community, Chincoteague shopping offers beach related souvenirs as well as ponies everywhere.  You can find beautiful shells at all the stores and are also sold on many front lawns throughout this community. There is fresh water taffy, fudge, jerky, kites and beach towels and clothing everywhere. Even the local pharmacy has a nice gift shop that is worth going to view.

Of the many shops to choose from, my favorites were The Brant, Pony Tails Candy Shop, Eclectic Beachcomber and Classy Hipsy.  Most of these shops are located either on Main Street or Maddox Blvd.  Island Foods Great Valve is the only grocery store on the island located on 6277 Cleveland Street, right off Main Street. Tom’s Cove Campground store also has some groceries as well as souvenirs and fishing equipment.

Water park on Chincoteague Island

Go to Maui Jack’s Waterpark

Maui Jack’s Waterpark located at 6742 Maddox Blvd. offers family fun during those hot summer days.  The park is open weekends at the beginning of May and daily from May 25 to September 22 from 10 to 6 pm. All day admission, if over 48” is $22.99, under 48” it’s $17.99 and kids under 3 are always free.  The park also offers late day passes (after 3 pm) for $18.99 and $14.99, respectively.

The park features three water slides, a lazy river, two side by side 32’ high-speed racer slides and a splash zone. They have complimentary sunscreen dispensers throughout the park and free life vests. You can rent a locker for your convenience as well as a cabana for your enjoyment. You can purchase food and souvenirs and they even offer a Bar and Grill with signature cocktails and grill food.

Go Fishing or Crabbing

There are fishing docks and piers located all over Chincoteague Island.  Surf fishing is also a popular sport here. They are numerous companies offering charter boats and fishing trips throughout the year.  Crabbing and clamming are very popular also on the island.

You can catch crabs with a net and baited line with anything on the end of it even chicken! The line needs to be long enough to sit at the bottom of the water, when you feel the crabs nipple at the bait you scoop in with your net and get them. Just remember crabs need to measure 5” from back shell point to point in order to keep them.

Clams are also plentiful in this area especially easy at low tide. The best way to calm is with a “clamming rack” in shallow water.  Dig the rack into the sandy water and you will then see the clams.  Another way is to look for signs in the sand, such as bubbles and by digging under the surface of the sand you will find the clams.

Eat Fresh Seafood

Coastal towns offer great fresh seafood and Chincoteague Island being by the Chesapeake Bay is known for crabs among other seafood favorites. There are many seafood restaurants to choose from.  Don’s Seafood Restaurant, Crusty Crab Seafood Shack, AJ by the Creek, The Crab Snack, The Water’s Edge, The Ropewalk, and Steamers Restaurant are all popular seafood restaurants.  Whichever you choose you won’t be disappointed.

We ate at The Ropewalk which has inside and outside dining right on the Chincoteague Channel. You can watch the stunning sunset while having dinner.  This restaurant offers an outside playground so families love this place. Although we enjoyed the atmosphere at this restaurant our food was served cold, however, the manager did try to make it up to us.

Sunset over Chincoteague Channel
Sunset over Chincoteague Channel

Take in the Sunset

The sunset is a site to see when visiting Chincoteague Island.  To watch the sunset you must be on the Chincoteague Channel which is by Main Street.  You can see this stunning sunset on a clear night from many restaurants and hotels located on the channel and also at Robert N Reed Waterfront Park also known as Love Park.

 Love Park, located at 4083 Main Street is a community park that has four huge Adirondack chairs spelling the word “LOVE”.  It’s a great place to take photos.  You can also see “Misty”, the status of the famous pony.  There is also a fishing pier with 10 boat slips and a pavilion.

Another park to see majestic sunsets at is the Donald J. Leonard Park located at 4586 Main St. This park also has picnic tables and kayak access. This park is pet-friendly.

At both of these parks, you can also see rocket launches from the NASA facility if you’re lucky to be in town when they have one.

Get up early to Watch the Sunrise

The sunrise is also stunning and can be seen on the Assateague Channel side of the island as well as at the beach on the Atlantic Ocean. At two of the campgrounds, the KOA and Tom’s Cove Campground you can wake up to this beautiful sunrise.  Also if you are staying anywhere on the Assateague Channel you can see the twin light of the Assateague Lighthouse at night.

Wallops Island/NASA Visitors Center

Wallop Island is the home to NASA Wallops Flight Facility which is located on your way to Chincoteague Island (6 miles). It’s the home to NASA facility and launch center. Although it’s not open for public tours, they have a visitor’s center that is open to the public Tuesday to Saturday from 10 am to 4 pm. Admission is free.

You can learn about the history of this facility and the programs that are conducted there.  This facility still launches rockets with the launch pad located 4 miles from the visitor’s center and you will have a clear view from the ground to the sky from there.  On major launch days, you would need to be at the facility 4 to 5 hours prior to the launch as it gets very crowded.

NASA Wallops Facility will launch a total of 8 rockets through a contract with Dulles VA Orbital Sciences Corporation to supply precious cargo to the International Space Station.  You can go to their website https://www.nasa.gov/content/nasa-wallops-visitor for approximate launch dates.

Take a Boat Ride/Pony Cruise

Another relaxing way to view the ponies is to take a Pony cruise. These cruises also give you the opportunity to see waterfowl and dolphins too. Boat cruise companies also operate sunset cruises, clamming and crabbing tours and charter fishing experiences.

Some of the places that offer these cruises are:

  • Daisy’s Island Cruises is opened year-round where small or large groups can experience pony, waterfowl, dolphin and local history. They have a permit from the National Park Service that allows them to operate on their shores. This gets you up close to the wildlife on the refuge.
  • Captains Barry’s Back Bay Cruises offers an eco-expedition with hands-on experience. The tours are limited to six passengers so you can interact with the environment. You get to dig in the mud and work crab pots. It’s just an overall different fun adventure. They also have an adult only champagne sunset cruise you may want to check out.
  • Captains Dan’s Around the Island Tours has cruises 3 times daily, depending on the season, that goes around the whole island of Chincoteague. They also have pony tours.
  • Assateague Explorer offers Pony Watching/Wildlife Cruises and well as sunset cruises aboard a larger vessel with a bathroom. These cruises are usually between 1 1/2 and 2 hours long.
  • Chincoteague Island Adventures, owned and operated by Captain Randy, offers a truly local experience of the area with a smaller (only 6 passengers boat) and personal touch as he was born and raised on the island.

Go to the Farmers Market

Every Saturday morning from 9 am to 1 pm, the Cultural Alliance runs the Chincoteague Farmers Market located at 6309 Church Street where you can purchase fresh goods. They have everything from fresh produce to fresh seafood and also arts and crafts and attic treasures. The farmers market is open from April 27 to October 26 and every Wednesday from June 12 to August 28 and on Tuesday, July 23.

On the Second Saturday of these months, Artful Flea Market is also at this location and runs from May to October.  This market offers arts, crafts, antiques, collectibles, and attic treasures.  They are open from 9 am to 2 pm.

For a small coastal town, the Cultural Alliance provides all kinds of wonderful activities in the community. Besides the farmers market, they also sponsor Music at the Dock, Movies in the Park, Monthly Coffeehouse with great musical talent and the Island Photo Contest to name a few. Check out their website at  www.chincoteagueca.org for events when you are visiting the area.

Chincoteague Festivals

Besides the Pony Swim (mentioned above), Chincoteague has several festivals throughout the year.

  • The Easter Decoy and Art Festival are Friday and Saturday before Easter. Carvers and artists from all over sell and exhibit their work. There is also a silent auction of pre-owned carvings.
  • The Seafood Festival happens the first Saturday in May at Tom’s Cove Park and features great local seafood along with music and dancing. An arts and craft show is also part of this festival.
  • The Blueberry festival features the largest fine arts and craft event on the eastern shore of Virginia, live music, breakfast and lunch and everything blueberry that you can think of! It’s the third weekend in July.
  • Labor Day Weekend is Decoy Carvers & Artists Association Decoy Show and the last Saturday in September is the annual Chili Chowder Cook-Off and Car Show sponsored by the fire department.
  • The first weekend in December, Main Street turns into an Old-Fashioned Christmas Parade with a special guest appearance from Santa Claus.

These are only some of the events offered by numerous organizations in Chincoteague.  For more details and other events contact the Chincoteague Chamber of Commerce at https://www.chincoteaguechamber.com/

Cook a Seafood Dinner

There are lots of seafood markets offering all types of fresh seafood every day.  Being near the Chesapeake Bay area, crab is everywhere.  Oysters and clams are also plentiful here too.  There are four places to purchase fresh seafood on the island.

We went to Gary Howard Seafood located on Deep Hole Rd for crab cakes and clams.  Other places include Ricky’s Seafood & Produce (Beebe Rd), Chincoteague Shellfish Farms (East Side Rd) and Little Bay Seafood Market (Chicken City Road). You can also purchase fresh seafood at the farmers market when it opened.

Go Kayaking or Canoeing

The Chincoteague and Assateague Channels are the perfect places to go kayaking or canoeing. There is nothing like being on the water to calm your soul. There are 5 town docks where you can launch. If you don’t have your own, you can rent at Snug Harbor Marina, Big Papa SUP, and Chincoteague Island Outfitters.

You can also take a kayak tour if that’s more your style. These tours are a great way to see the ponies too. Tours are offered by Assateague Explorer, Chincoteague Kayak Tours, Chincoteague Nature Tours, and Snug Harbor Kayak Tours.

Chincoteague Fire Department Carnival Days

The Chincoteague Volunteer Fire Department has permanent carnival grounds on Main Street where every year their annual carnival runs every Friday and Saturday (closed on Sunday) from the last weekend in June through the end of July and every day from July 22 to July 27. Its also opened July 3rd and 4th. It’s fun for the whole family with carnival rides, food, art & crafts, raffles, and games.

Other Things to do on Chincoteague Island

The Island Theater is located at 4074 Main Street. It’s a single screen theater offering current movies. They also have special movie nights showing old classics.

Funland Amusement’s located at 6528 Maddox Blvd. has family fun for everyone. Play miniature golf, take a ride in a go-cart or bumper boat and play arcade games.  They even have a kids merry go round and rock wall.

Libertino Lanes is the only bowling alley on the island. Its located at 3649 Willow Street.  It’s something to consider especially on a rainy day.

Accommodations on Chincoteague Island

When visiting Chincoteague Island there are several different types of accommodations you can choose from. We are campers and stayed at one of the three privately owned campgrounds on the island.  (Note: they are no public campgrounds). They are many hotels and motels on the island with prices ranging from $75 to $400 with many different amenities covering all your needs. You could also choose from 4 Bed and Breakfast Inns with price ranges of $125 to $275 per night.

If you are staying a week or longer there are several vacation house rental agencies offering multiple bedrooms and amenities to cover all your vacationing needs.  You can contact the Chincoteague Chamber of Commerce for a list of all available accommodations at  https://www.chincoteaguechamber.com/.

As you can see, from all of the above activities there are a lot to choose from when visiting Chincoteague Island so go and enjoy your trip. What are your favorite places to see?

Sunrise and sunset over Chincoteague Island Virginia

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14 thoughts on “The Ultimate Guide to Chincoteague Island VA”

  1. My brother’s family just spent a week there. They go annually. It’s on my list to visit. Thanks for a great overview of Chincoteague! It sounds just perfect!

  2. OMG! You did get a lot into this post! I loved reading it and it was in fact, one of the best things I read today.
    Who doesn’t love Mr Whimpy! It’s so popular here in the UK too.
    Your photos are gorgeous too. I wish …
    Must add to my bucket list.

  3. I just posted a similar post on my blog. We visit almost every summer, and absolutely love bringing our kids there!

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