There is something extra special about Chincoteague in May - the scent of salt in the air, the sound of shorebirds returning, and the energy of the island reawakening for the season. If you’re planning a spring escape, this 3-day itinerary hits all the local favorites and hidden gems, from the beloved Chincoteague Seafood Festival to peaceful beach walks, sweet treats, and cozy comforts at The Refuge Inn, your home away from home!
Friday: Check In, Explore & Dine by the Water
Arrive in town and check in at The Refuge Inn, your peaceful island home for the weekend. Once you’re settled, head out to explore either with a beach walk, a stroll through the nearby Chincoteague National Wildlife Refuge, or a visit to the Museum of Chincoteague Island (open Friday and Saturday from 10 AM to 4 PM). The museum is a local gem, perfect for diving into the island’s rich history, learning about the wild ponies, and seeing Misty of Chincoteague’s original model.
As evening sets in, enjoy dinner at The Village Restaurant, a long-time favorite for waterfront views and fresh seafood. We recommend the crab imperial, crab dip, or seafood platter paired with a sunset, of course.
After dinner, head to Mr. Whippy’s for a nostalgic soft-serve swirl to cap off your first evening on the island.
Saturday: Festival Day, Island Exploring & Local Favorites
Start your Saturday with a local coffee stop like Main Street Coffee House, Amarin, or AM PM Wine & Gourmet Market, then make your way to Tom’s Cove Park for the annual Chincoteague Seafood Festival. Running from 10 AM to 4 PM, this event brings together steamed clams, shrimp, oysters, crab cakes, hush puppies, and more plus live music and a lively community atmosphere.
Prefer a quieter Saturday? Revisit the Museum of Chincoteague, take a longer walk through the wildlife refuge, or book a boat tour with Cowboy Cruise Company or Daisey’s Island Cruises to see the wild ponies and explore Chincoteague’s scenic waterways.
That evening, enjoy a casual but unforgettable dinner at Captain Zack’s Seafood, a local favorite known for its famous Bloody Marys, oyster po’ boys, and killer seafood specials. Whether you go for the scallop Caesar wrap, fish tacos, or just see what’s on the board, you really can’t go wrong.
After dinner, walk or drive over to the Island Theatre, where Conclave is playing at 7 PM - a classic small-town movie night in a beautifully preserved historic setting.
Sunday: Donuts, Bike Rides & Sweet Treats
Sunday morning means one thing: Sandy Pony Donuts! Recently reopened for the season, this island staple offers hot, made-to-order donuts in fun flavors like maple bacon, s'mores, and blueberry pancake. Grab a dozen and enjoy them out on the porch at The Refuge Inn, or take them to go for a scenic start to your day.
After breakfast, rent bikes right on-site at The Refuge Inn’s Bike Depot and cruise through the Chincoteague National Wildlife Refuge. This peaceful, protected area is full of winding trails, birdwatching opportunities, and quiet spots to pause and soak in the natural beauty of the island. It's one of the best ways to experience Chincoteague in spring, no car needed.
When you’re ready for lunch, you have two can’t-miss options:
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Better. food truck, known for fresh, creative bites and a laid-back local vibe
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Pico Taqueria, a Chincoteague favorite for bold, delicious tacos made with local ingredients and island flair
Then satisfy your sweet tooth at Island Creamery, consistently ranked among the best ice cream shops in the nation. It’s the perfect final treat before wrapping up your trip.
Take a walk on the beach or spend your last afternoon birdwatching in the Wildlife Refuge, where you might spot egrets, herons, and maybe even a bald eagle. There is an eagle's nest visible along the Wildlife Loop, off to the right about 1/2 mile in.
For your final evening, order takeout pizza from Famous Pizza or Cosa Pizza, and enjoy a relaxing night in. Whether you unwind with a swim in the indoor pool, warm up in the sauna, curl up with a good book, or watch the sunset from your balcony at The Refuge Inn, it’s the perfect way to reflect on a weekend well spent.
Monday: Breakfast In & Goodbyes
On your final morning, enjoy a cozy farewell with The Refuge Inn’s complimentary in-room breakfast delivery. There’s nothing better than sipping fresh coffee and enjoying a nice breakfast from the comfort of your room as you reflect on a weekend full of great food, coastal charm, and island memories. May is one of the most magical months to experience Chincoteague. With spring in full swing, local businesses reopening, and signature events like the Seafood Festival, it’s the perfect time to enjoy everything the island has to offer, made even better with a stay at The Refuge Inn.