Espresso Boarding: Islands of Chincoteague, Assateague
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Islands of Chincoteague and Assateague:
Wild horses, ocean waves, beach bonfires
This week, we will explore the islands made famous by the story of Misty of Chincoteague. Imagine a place where you can play outdoors in the presence of wild horses and then enjoy soft shelled crabs and a beach bonfire.
You can choose your ideal itinerary based on your desire for Adventure, Culture, or Relaxation. These itineraries are handy to bookmark - a blister or torn muscle may convert your Adventure plans into Relaxation plans. Let’s get started.
- Cris
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Arrival and Exploration of Chincoteague | Assateague Island Adventure | Water Sports and Wildlife | Hiking and Final Exploration |
ADVENTURE!
Day 1: Arrival and Exploration of Chincoteague
Head to the Chincoteague National Wildlife Refuge for a day of hiking and taking pictures of the famous wild ponies. This is one of the few places in the US where you can see wild ponies - it’s not a zoo. Stay away from them and definitely don’t try to feed them. Pictures are great. If you see baby ponies (foals), give extra space because those parents are protective.
Rent a kayak or paddleboard to explore Assateague Channel. This gives you a chance to see the ponies from the water and savor hope for the future of the planet. You could also bicycle along Beach Road during sunset, ending your ride at Assateague Island. This is better than driving along a coast in a convertible with the top down. You are one with nature. This is the ultimate digital detox for day one of a vacation.
Day 2: Assateague Island Adventure
Start early with a sunrise walk on Assateague Beach. Morning yoga (or coffee) are traditions here. Then head to Assateague Island National Seashore and rent a fat-tire bike to cover the island’s paths. This brings you up close to all of the nature on the island. You are visiting their home and so be quiet, respectful, and leave no trash or damage behind. Horses can get sick from human food. Those that learn to come up to the road to beg for food are often hit and killed by cars. Visitors are kicked, bitten and knocked down every year as a direct result of getting too close to the wild horses. Protect your family by respecting theirs.
In the afternoon, go for a horseback riding tour (these aren’t the wild horses) along the beach or through the marshes. While tours cater to all experience levels, I personally wouldn’t recommend learning to ride here. You are surrounded by wild nature so even seasoned tour horses can get spooked. Yeah…that means a ‘holy crap!’ moment when the horse bolts and runs uncontrollably until someone saves you (unless you know how to ride).
Still have energy? Enjoy a sunset boat tour along the islands for a chance to see dolphins and more wild ponies as the day winds down. I have not personally seen dolphins play with the ponies but other people swear they have seen foals swim into the ocean and play with the dolphins.
Day 3: Water Sports and Wildlife
Spend the morning on a guided paddleboard or kayaking tour of the Chincoteague Bay. Some tours even offer eco-tours, teaching you about the local ecosystem and marine life. The tours are recommended because they teach you about hidden waterways, places where snakes can be a problems, and any current information about tides and undertows. This is important for your afternoon adventure.
During the afternoon, go kite surfing! This is a great place to learn from guides. Experiences surfers can rent the equipment and dare people to wipe that grin from your face. The island has a few great seafood restaurants to refuel before hanging out on the beach to stargaze. You came here to connect with nature and that includes a sky full of stars.
Day 4: Hiking and Final Exploration
Hike the Woodland Trail on Chincoteague Island. This trail takes you through forests that are filled with birds - bring your binoculars (and your mosquito spray). If you haven't had enough of the ponies, this trail often offers sightings. Never approach a foal and give all horses some respectful space. If they stampede then get out of the way!
End your trip with a bonfire on Assateague (Assateague allows bonfires in designated areas). Relax and enjoy your final night by the ocean.
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Exploring Chincoteague's Heritage and Local Culture | Wildlife, History, and Art on Assateague Island | Island Ecology, Historical Stories, and Artisan Crafts | Environmental Awareness |
CULTURE!
Day 1: Exploring Chincoteague's Heritage and Local Culture
Spend the morning at the Chincoteague Island Museum of History to learn about the island’s origins, from the Native Americans to the arrival of European settlers.
The exhibit about Misty of Chincoteague, the beloved pony made famous by Marguerite Henry’s novel, will capture the attention of children (or people who read the book as a child).
During the afternoon, stroll through downtown Chincoteague to see the galleries, shops, and homes that are the current culture of the island. Is your home decorated in a beach theme or a country theme? You will find hand carved ducks, paintings of birds, and beach decor. My personal favorite is the sea glass jewelry made from local sea glass by Gertraud Fendler.
Do you consider ice cream to be culturally significant? Me too! Find your favorite flavor, based on local ingredients, at the Island Creamery.
Day 2: Wildlife, History, and Art on Assateague Island
Start at the Assateague Island Visitor Center to learn about the island’s ecosystems, history, and the Assateague ponies. This is a great designated meetup point if your groups gets separated and has clean bathrooms.
Wildlife Loop
Bike along the Wildlife Loop to view the famous Assateague Ponies in their natural habitat. You can also drive along this loop but cars and horses should be kept far apart.
Assateague Lighthouse
Visit the historic Assateague Lighthouse, built in 1867. It’s a cultural and historical landmark for both islands, with stunning views of the surrounding landscape.
Day 3: Island Ecology, Historical Stories, and Artisan Crafts
Take a tour of one of Chincoteague’s historic homes, such as the Captain Timothy Hill House, which dates back to the 1800s. Learn about the maritime history and early settlers of the island. As you look for walk-in closets (don’t exist) and his-and-hers bathroom sinks (ha! not here), you will ponder how much space we really need to be content and happy.
Beach Bonfire
Spend a peaceful evening on Assateague Island Beach with a beach bonfire. This is a great way to connect with the natural beauty of the area, unwind, and enjoy stargazing in the dark skies of Assateague. The culture of these islands is centered around preservation and protection of the horses, birds, plants, and non-human wildlife that is privileged to live here. This is also a memory that your spouse and children will cherish. Roasting marshmallows, noticing the stars, and just talking with each other could be quite novel.
Day 4: Environmental Awareness
Capture images of wild ponies, birds, and coastal scenes during a guided Wildlife Photography Walk through Assateague Island. Learn the names of the many birds and receive tips on how best to photograph them. Your friends will think that you borrowed someone else’s photos because they look so good. Serious photographers (or people who want to learn) may prefer the 3-day photography experience.
| Day 1 | Day 2 | Day 3 | Day 4 |
|---|---|---|---|
| Settle In and Enjoy the Island Vibe | Connecting with Nature | Spa Day! | Slow-Paced Morning and Departure |
Relaxation
Day 1: Settle In and Enjoy the Island Vibe
The next four days are about being fully present, connecting with Nature, and opening quiet space to reconnect with your family. Once you check into your BnB, open the windows, step onto the porch, and breathe deeply. That island air is healing. Connect your phone to the charger and commit to pretending it’s 1990 and email does not exist. Spam is still a meat in a metal container. Meetings can’t easily be dropped into your calendar, forcing you to attend or justify your absence.
Feel better? Me too.
Now that you are settled, stroll through the streets of Chincoteague to get a sense of the area. Wander down to the water and allow the waves to tickle your feet. Imagine how life felt when every minute of the day wasn’t triple booked.
Day 2: Connecting with Nature
Beach Yoga on Assateague Island
Stretch those muscles with beach yoga on Assateague Island. This is a family destination and so all experience levels are welcome. You may even encounter a family that can’t stop laughing because ‘their muscles don’t twist that way.’ It’s polite to tip your instructor $5.
Wildlife Loop
njoy watching the wild ponies, herons, or egrets during a relaxing walk around Wildlife Loop on Assateague Island. Bring your journal with you to take notes of great ideas that occur to you during the stroll. It’s a long tradition for people to get their best inspiration in places where it’s tough to take notes so be prepared - who knows what brilliant idea will come along?
Day 3: Spa Day!
Treat yourself to a spa day at Natural Elements Spa in Chesapeake. Popular treatments include the Swedish massage or hot stone treatment. Personally, I find it difficult to choose only one treatment. That would be like choosing your favorite child. It’s easy to fill most of a day here, particularly since you need to drive a short distance into Virginia.
Day 4: Slow-Paced Morning and Departure
Head out for a morning walk on the beach and take deep breathes. You are relaxed, centered, and surrounded by a calm family. Enjoy this moment.
How is it day four already? You have lots of notes in your journal, photos, and memories with your children. It’s ok to feel a little grumpy about returning to work but you can take your rebalanced perspective with you.
Chincoteague Island
$: The Sea Star Cafe is your place to enjoy crabcake sandwiches on the patio, admiring the view. They focus on local ingredients and have a great selection of foods so you can eat “healthy” (or not). The entire menu is available for carryout (something you should not assume at other places). I wish this place was a block from my home.
$$: The Village Restaurant is a casual seafood spot with beautiful views, overlooking the Chincoteague Bay. Their dishes are simple, fresh, and capture the essence of Chincoteague’s seafood. The soft-shelled crabs, when in season, can justify a fairly lengthy wait to be seated. Yum.
$$: Don’s Seafood Restaurant is a great place to get your kids to try new foods without feeling as though you just wasted your money. The food is good (so you are happy to eat what the kids reject) and fairly priced (making it ok to order an adult meal for an 8-year old). Their menu is based on what is in season (so really fresh).
$$$: Bill's Prime Seafood & Steaks is the perfect blend of fine dining and a relaxed island atmosphere. The Crab Cakes and Filet Mignon are the most popular. Locals swear by the clam chowder.
$$: Comfort For Families
The Refuge Inn offers cozy, comfortable rooms, many with private balconies. The hotel has a heated indoor pool, a fitness center, and a bike rental service. Guests love its location and family-friendly atmosphere.
Near: Chincoteague National Wildlife Refuge and the beach.
Pro: On-site bike rentals eliminate the need to bring them with you.
Con: Rooms can fill up quickly during peak seasons so you need to plan ahead.
The Channel Bass Inn is a charming bed-and-breakfast with beautifully landscaped gardens and afternoon tea. The quiet setting offers a relaxed experience while still being close to the island’s attractions.
Near: 2-3 Blocks from the ocean.
Pro: It’s quiet, providing space for conversation or reading.
Con: With (intentionally) few rooms, it’s not the place to stay if you are looking for a party atmosphere.
The Island Resort has spacious rooms and private balconies overlooking Chincoteague Bay. This is a rare Inn that offers both smoking and non-smoking rooms and so it’s a good idea to confirm in advance if you have a preference.
Near: Waterfront!
Pro: Watch the sunset over the water from your personal balcony.
Con: It’s a bit of a walk to find food if you don’t want to eat in their restaurant.
$: Clean and Safe
The Waterside Inn offers affordable rooms with waterfront views, fishing from the private pier, and a quiet location close to shops and restaurants.
Near: Waterfront!
Pro: Great for for fishing enthusiasts.
Con: The rooms are simple and can feel outdated.
The Brant
The Brant offers a great collection of paintings of the local landscapes, beach-inspired home décor, and jewelry made from local artists.
The Egret Moon Artworks
I love the Egret Moon ArtWorks for their useful (and artistic) pottery with ocean-inspired designs. Keep an eye out for mugs, bowls, and vases featuring natural, coastal colors. If you are lucky enough to see one of their ‘transmuting fire’ paintings then I would suggest you grab it. These are in high demand because they are quite beautiful.
Captain Steve's Bait and Tackle
Sunscreen, bug spray, fishing rods, bait…Captain Steve’s Bait and Tackle has everything that you forgot to bring with you. Most people find themselves stopping in here. They also rent cottages if you need a place to stay. It can also be a place to pick up a t-shirt for the kids.
Blue Crab Treasures
This is a classic beach shop where you can find coastal-themed decor, handmade jewelry, and small gifts to take home. Their playing cards that feature the local horses will be a hit with anyone who has recently watched or read Misty of Chincoteague.
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