Chincoteague Island Events

North Herd Roundup

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The North Herd Roundup will take place July 26th, as the Saltwater Cowboys ride across the northern end of Assateague Island, to herd between 100-150 ponies. This roundup is not open to the public for the safety of the ponies and the public. ...

Beach Walk

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One of the most beautiful events of an already beautiful week, the Beach Walk has become a favorite of the Seaside family. The Saltwater Cowboys will release the North Herd of ponies at daybreak, and walk them along the shore of the Atlantic to join the South Herd in the South Corral.  The wildlife refuge opens at 5AM, and attendees are advised to arrive as early as possible for parking purposes....

Vet Checks & Buyback Selection

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Make your way to the South Corral to see the Chincoteague Ponies receive their vet checks prior to the Pony Swim. Buybacks for the year are also selected this day.

101st Annual Pony Swim

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The Main Event. Chincoteague's world famous Pony Swim will take place Wednesday, July 29th at slack tide as we begin another century of tradition. View the Pony Swim on the big screen with thousands of other pony lovers at the Veteran's Memorial Park, or make your way through the Marsh and witness the event front row from Pony Swim Lane!...

Chincoteague Pony Auction

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Dreams will come true at 3648 Main Street as the foals born throughout the year are auctioned off with proceeds benefiting the Chincoteague Volunteer Fire Company. Viewers and bidders are allowed to enter beginning at 6 AM. Any chairs placed prior to then will be removed by law enforcement. ...

Swim Back

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The Saltwater Cowboys parade the South Herd on the reverse Parade Route so they can swim back to Assateague Island as Pony Swim week concludes.

Music at the Dock: Backroad

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Get ready for another unforgettable summer on the island! The Chincoteague Cultural Alliance and Seaside Vacations & Sales are teaming up once again to bring guests and locals a beloved summer tradition, a series of FREE waterfront concerts at Robert Reed Downtown Waterfront Park. Set against the stunning backdrop of the bay, this concert series offers the perfect opportunity to gather with friends and family, soak in breathtaking sunsets, and enjoy incredible live music from talented regional performers. Whether you’re visiting for a week or taking a long weekend, these concerts are a must-experience part of Chincoteague’s warm-weather charm. Full 2026 Summer Concert Schedule July 4: Salisbury Community Band July 11: Southern Frog July 25: Randy Lee Ashcraft and the Saltwater Cowboys August 1: Backroad August 15: Island Boys August 29: Bobby BlackHat Band September 6: C.A.I.S.O. Guests are encouraged to circle these dates on their calendars, grab some lawn chairs or a blanket, and settle in for evenings filled with great music, dancing, and unbeatable waterfront views. There’s simply nothing like listening to live music while the sun sets over the bay and the salty island breeze rolls in....

Music at the Dock: Island Boys

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Get ready for another unforgettable summer on the island! The Chincoteague Cultural Alliance and Seaside Vacations & Sales are teaming up once again to bring guests and locals a beloved summer tradition, a series of FREE waterfront concerts at Robert Reed Downtown Waterfront Park. Set against the stunning backdrop of the bay, this concert series offers the perfect opportunity to gather with friends and family, soak in breathtaking sunsets, and enjoy incredible live music from talented regional performers. Whether you’re visiting for a week or taking a long weekend, these concerts are a must-experience part of Chincoteague’s warm-weather charm. Full 2026 Summer Concert Schedule July 4: Salisbury Community Band July 11: Southern Fog July 25: Randy Lee Ashcraft and the Saltwater Cowboys August 1: Backroad August 15: Island Boys August 29: Bobby BlackHat Band September 6: C.A.I.S.O. Guests are encouraged to circle these dates on their calendars, grab some lawn chairs or a blanket, and settle in for evenings filled with great music, dancing, and unbeatable waterfront views. There’s simply nothing like listening to live music while the sun sets over the bay and the salty island breeze rolls in....

National Park Free Entrance Day

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Make your way to Chincoteague to experience a FREE day on the National Wildlife Refuge to celebrate the 110th Birthday of the National Park Service ! Head down beach road to see if you can spot the wild ponies roaming, catch a sunrise over the Atlantic Ocean (or sunset over the bay( or hit the trails for some exercise! ...

Music at the Dock: Bobby Black Hat

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Get ready for another unforgettable summer on the island! The Chincoteague Cultural Alliance and Seaside Vacations & Sales are teaming up once again to bring guests and locals a beloved summer tradition, a series of FREE waterfront concerts at Robert Reed Downtown Waterfront Park. Set against the stunning backdrop of the bay, this concert series offers the perfect opportunity to gather with friends and family, soak in breathtaking sunsets, and enjoy incredible live music from talented regional performers. Whether you’re visiting for a week or taking a long weekend, these concerts are a must-experience part of Chincoteague’s warm-weather charm. Full 2026 Summer Concert Schedule July 4: Salisbury Community Band July 11: Southern Fog July 25: Randy Lee Ashcraft and the Saltwater Cowboys August 1: Backroad August 15: Island Boys August 29: Bobby BlackHat Band September 6: C.A.I.S.O. Guests are encouraged to circle these dates on their calendars, grab some lawn chairs or a blanket, and settle in for evenings filled with great music, dancing, and unbeatable waterfront views. There’s simply nothing like listening to live music while the sun sets over the bay and the salty island breeze rolls in. ...

Music at the Dock: C.A.I.S.O.

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Get ready for another unforgettable summer on the island! The Chincoteague Cultural Alliance and Seaside Vacations & Sales are teaming up once again to bring guests and locals a beloved summer tradition, a series of FREE waterfront concerts at Robert Reed Downtown Waterfront Park. Set against the stunning backdrop of the bay, this concert series offers the perfect opportunity to gather with friends and family, soak in breathtaking sunsets, and enjoy incredible live music from talented regional performers. Whether you’re visiting for a week or taking a long weekend, these concerts are a must-experience part of Chincoteague’s warm-weather charm. Full 2026 Summer Concert Schedule July 4: Salisbury Community Band July 11: Southern Fog July 25: Randy Lee Ashcraft and the Saltwater Cowboys August 1: Backroad August 15: Island Boys August 29: Bobby BlackHat Band September 6: C.A.I.S.O. Guests are encouraged to circle these dates on their calendars, grab some lawn chairs or a blanket, and settle in for evenings filled with great music, dancing, and unbeatable waterfront views. There’s simply nothing like listening to live music while the sun sets over the bay and the salty island breeze rolls in. ...

Fall Roundup 2026

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The Chincoteague Volunteer Fire Company's Fall Roundup will take place September 25th (South Herd) and 26th (North Herd) to perform health checks on our beloved ponies, and to identify any foals that have been born since July's Pony Swim.  The South Herd Roundup on Friday takes 1-2 hours, and spectators are invited to watch from Beach Road or from the corral.  Saturday's North Herd Roundup takes 5-6 hours. Spectators are allowed to walk up to the cattle grate at anytime of day, but access further north is restricted until the Roundup is complete for the safety of everyone involved....

Endless Summer Cruisin' 2026

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The 29th annual Endless Summer Cruisin' will take place October 8th-11th in conjunction with annual Hot Rod & Custom Car Show, making it THE place to be for car enthusiasts of all ages!  Boardwalk Cruises, celebrity appearances, and LED light car show, live music and more highlight the weekend with over 500 trophies, plaques, and awards presented....

2026 Oyster Festival

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Celebrate the beginning of oyster season with a day filled with fun, friends, and food! Enjoy all you can eat seafood, live music from Island Boy, and Extravaganza Raffle, and a Best Space contest that brings so much joy and creativity to the event.  Gates will open at 10:00 AM, with appetizers being served at 11, and seafood tents opening at Noon.  Tickets for the Seafood Festival are $65 per person (Children under 5 are FREE!) and can be purchased on the Chincoteague Chamber of Commerce website...

National Wildlife Refuge Week

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Kick off National Wildlife Refuge Week with a day of FREE entry onto the refuge! Head down beach road to see if you can spot the wild ponies roaming, catch a sunrise over the Atlantic Ocean, or hit the trails for some exercise! ...

National Park Free Entrance Day

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Make your way to Chincoteague to experience a FREE day on the National Wildlife Refuge in honor of Theodore Roosevelt's Birthday! Head down beach road to see if you can spot the wild ponies roaming, catch a sunrise over the Atlantic Ocean, or hit the trails for some exercise! ...

National Park Free Entrance Day

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Make your way to Chincoteague to experience a FREE day on the National Wildlife Refuge in honor of Veteran's Day! Head down beach road to see if you can spot the wild ponies roaming, catch a sunrise over the Atlantic Ocean, or hit the trails for some exercise! ...

Ocean City Running Festival

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Get ready to hit the pavement and enjoy the scenic beauty of Ocean City and beyond at the Ocean City Running Festival, now in its fourth year! This exciting festival offers a variety of race options for runners of all levels: 5K 8K Half Marathon Full Marathon Participants will enjoy beautiful, scenic routes that take them along the coast and as far as Assateague State Park, providing unforgettable views of the ocean, wildlife, and the natural beauty of the area. ...