Ready for an unforgettable escape to Virginia’s Eastern Shore? Chincoteague Island is the perfect destination for a long weekend filled with wild ponies, fresh seafood, peaceful sunsets, and charming local spots. Whether you’re craving outdoor adventure or relaxing waterfront views, this four-day Chincoteague itinerary has it all — and the best part is, you can stay right on the bay at Chincoteague Bay RV Resort & Cottages.
Day 1: Arrive and Settle in at Chincoteague Bay RV Resort & Cottages
Kick off your getaway by checking into Chincoteague Bay RV Resort & Cottages, your home base for the weekend. Choose from waterfront cottages, spacious RV sites, or waterfront glamping tent sites, all just minutes from downtown Chincoteague and the Assateague National Seashore.
After settling in, take a stroll along the resort’s private shoreline or lounge by the pool. You’ll find plenty of on-site amenities like a swimming pool, fishing pier, and sport courts — perfect for families, couples, and friends looking to unwind.
Explore our resort amenities here.
Day 2: Assateague Adventures & Chincoteague’s Famous Ponies
Morning: After breakfast, head to Assateague Island National Seashore, just a short drive from the resort. Spend the morning relaxing on the beach, searching for seashells, and maybe even spotting wild ponies along the shoreline.
Next, visit the Chincoteague National Wildlife Refuge. Hike the Wildlife Loop Trail (walk or bike rentals available nearby) for a chance to see herons, egrets, and the famous Chincoteague ponies grazing in the marsh.
Afternoon:
Cool off with a treat at Island Creamery — consistently voted one of the best ice cream shops in the country.
Dinner:
Enjoy fresh local seafood at Bill’s Prime Seafood & Steaks or the waterfront Ropewalk Chincoteague, both offering kid-friendly menus and outdoor dining.
Day 3: Wildlife, Waterpark, and Sunset Cruises
Start your day with a cup of coffee on your cozy cottage porch or RV site, soaking in serene waterway views—keep an eye out for dolphins! Feeling adventurous? Launch your kayak or paddleboard right from our onsite access and explore the beauty beyond.
Afternoon:
After some outdoor adventure, head back to Maui Jack’s Waterpark for a fun-filled afternoon. Enjoy the slides, splash pads, and lazy river — perfect for kids and adults to cool off and relax. Don’t forget – all Chincoteague guests receive a waterpark discount! Stop by the Chincoteague Bay Resort front desk for questions or to purchase tickets.
Evening: Cap off the day with a sunset dolphin-watching cruise with Daisey’s Island Cruises. Watching the sun dip below the horizon while dolphins swim nearby is a highlight of any Chincoteague visit. Alternatively, rent a pontoon boat or jet skis through Sea Rocket Adventures, where Chincoteague Bay guests can enjoy a 10% discount!
Day 4: Local Breakfast & Check-Out
Before heading home, stop for a hearty breakfast at Mister Whippy (known for its nostalgic diner vibe and soft-serve ice cream) or the local-favorite Beach Road Round-Up for a casual, satisfying meal.
After breakfast, check out of Chincoteague Bay RV Resort & Cottages and start planning your next visit — whether it’s for the annual Chincoteague Pony Swim, a fall fishing trip, or a relaxing Second Summer stay in September.
Plan Your Chincoteague Bay Getaway
Whether you’re a nature lover, foodie, or beachgoer, Chincoteague Bay RV Resort & Cottages is the perfect basecamp for your long weekend escape. As you can see, it’s hard to fit all that Chincoteague has to offer into even a long weekend. Take advantage of our 3-, 5-, or 7-night special offers and save up to 25% on your stay! Plan your Chincoteague escape today.
Check our special offers and book your stay now.
Summary of Things to Do, Eat, and Places to Visit in Chincoteague:
Things to Do:
- Assateague Island National Seashore: Relax on the beach, explore the shoreline, or spot wild ponies.
- Chincoteague National Wildlife Refuge: Hike the Wildlife Loop Trail and experience nature firsthand.
- Island Creamery: Enjoy delicious homemade ice cream in a cozy, local spot.
- Kayaking & Paddleboarding: Rent from Chincoteague Bay Adventures or Snug Harbor Marina to explore the bay.
- Maui Jack’s Waterpark: Cool off with fun water attractions like slides and a lazy river.
- Daisey’s Island Cruises: Go on a sunset dolphin-watching cruise.
- Sea Rocket Adventures: Rent a pontoon boat or jet skis and enjoy a 10% discount for Chincoteague Bay guests.
Where to Eat:
- Bill’s Prime Seafood & Steaks: Enjoy fresh seafood and waterfront views.
- Ropewalk Chincoteague: A waterfront dining spot with local seafood and casual fare.
- Mister Whippy: A nostalgic diner with soft-serve ice cream and hearty breakfast options.
- Beach Road Round-Up: A local favorite for breakfast with a casual and satisfying menu.
Places to Visit:
- Chincoteague Bay RV Resort & Cottages: Your ideal base for relaxation, with waterfront access and plenty of activities.
- Assateague Island National Seashore: A must-visit for nature lovers and beachgoers alike.
- Chincoteague National Wildlife Refuge: Perfect for hiking and wildlife watching with a historic lighthouse.