20 Awesome Chesapeake Bay Things to Do in June 2019

Posted on June 03 2019

20 Awesome Chesapeake Bay Things to Do in June 2019

June came up fast, didn’t it? By now you’ve probably planned your summer calendar, eaten at least two dozen crabs and gotten reacquainted with your favorite dock bar—but the Chesapeake Bay is just warming up. Here’s how to make the most of the official start of Chesapeake Bay season.

  1. Try Arlington’s new food market spot, Quarter Market. The Local Oyster is an expansion of Baltimore’s Mt. Vernon Marketplace and has the best steamed seafood selection.
  2. View some of Chesapeake Bay Regions most notable gardens during the Garden Dialogues 2019: Washington, DC, and Fairfax, VA by The Cultural Landscape Foundation on June 8.
  3. Venture over the Chesapeake Bay to the Eastern Shore to view the world famous wild horses at Assateague Island located in Maryland and Virginia. The wildlife tour or kayaking is a great way to see much of the refuge and its wildlife by boat or kayak.
  4. Tour the. Frederick Designers Show House featuring Keyser Interiors, Patrick Street Interiors and Tuscan Blue Design, in Frederick, MD on June 13-23. The showhouse benefits the Weinberg Center for the Arts.
  5. Pie. Just one word to make your day. Like a scene in Waitress.  For the best pie, visit South County Café in Deale, MD.  It is just south of Annapolis and north of Chesapeake Beach.
  6. Let the team at The Giving Tree Spa in Williamsburg, VA help you relax and kick start your summer skin routine. Bring your significant other and enjoy a couples massage or get a Dead Sea Chamomile Masque.
  7. Go Patriotic! We mean the Virginia Beach Patriotic festival complete with military exhibits and great concerts on June 1-3.  
  8. Dock bars are a Chesapeake Bay tradition. Each one has its specialty food and views. This month we will highlight some boaters favorite:  Davis’s Pub in Eastport, MD and The Shanty in Cape Charles.  Sailors (Drinkers) don’t call Davis’s a bar they call it an institution!
  9. Take in one of the stunning (and free) waterfront Sunsets on the River concert series at the Hermitage Museum & Gardens .
  10. Experience a rebirth of an 1898 original bayside boarding house in Tilghman Island at the Wylder Hotel on the Eastern Shore of the Chesapeake Bay.
  11. Get your soccer (futbol) on at the North American Sand Soccer Championships. Elite athletes from 20 states and 7 different countries showcase their skills right here in the Chesapeake Bay Region.
  12. Rock out at Norfolk’s’ only rooftop beer garden. The Grain with live music Wednesdays through Sundays.
  13. Love to be a Chesapeake Bay skipper jack? How about a mariner?  Then join Sail Nauticus weekly in Norfolk on Wednesday and Saturday to learn how to sail.
  14. Cheers and then sip at 5th Annual Baltimore Wine Fest on the Canton Waterfront June 15th.
  15. Grab your suit for the 4 miles Great Chesapeake Bay Swim on June 9.
  16. Make a day to visit the Nations Capital and be sure to .visit the National BBQ battle. It is a lip smacking time on June 23-24.
  17. Get your inner sailor on and celebrate Norfolk Harborfest, the longest running, free maritime festival on the Chesapeake Bay celebrating its 42nd year.
  18. Not that you need an excuse to eat strawberries in June, but Ashland Strawberry Faire is as good a reason as any.  
  19. Make s’mores around the fire at while camping at Rocky Point State Park on Hart Miller Island in the middle of the Chesapeake Bay.
  20. Stick your toes while enjoying the Logstradamus Surf and Music festival in Virginia Beach on June 14-15.


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