Top 10 Summer Activities in Maryland

Summer is one of our favorite times of the year. The foliage and flowers are in full bloom, the weather is fantastic and the adventures to enjoy are plenty. Below is our list of the top 10 adventures to enjoy throughout the Eastern Shore. Join us at our top-rated waterfront Maryland bed and breakfast and use it as your home base while you check these memorable activities off your bucket list. This summer is THE summer to enjoy an Eastern Shore getaway you won’t soon forget.

Sailing on the Eastern Shore Maryland - Sailboat

1. Sail the Chesapeake with Blue Crab Chesapeake Charters

If you have not enjoyed a sunset cruise on the Chesapeake Bay, you are missing out. The Blue Crab Chesapeake Charters offers incredible sailing services April to the end of October on their 43-foot sailboat. Cruises are generally 90 minutes and they provide drinks. Longer cruises are an option but you need to contact them for a quote. Grab your sunscreen and enjoy a romantic and relaxing adventure on the water.

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Chester River Trading Company - Cruising MD

**Photo From Chester River Packet Co.

2. Cruise the Chester River

Enjoy cruising the Chester River with Chester River Packet Co. Thursday-Sunday. This cruise is for patrons that want to enjoy a little more on the ship as they offer a cash bar and dining/brunch options on certain days. Reservations are required for these popular cruises and they will not disappoint.

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Couple Golfing in Maryland - Eastern Shore

3. Enjoy Friendly Competition on the Golf Course

Nothing says “I love you” like duking it out on the golf course. There are three fun public golf courses to consider for your adventures on the greens. Dust off your clubs, put on your game face and enjoy the incredible grounds and award-winning public courses in Maryland.

  • Rocky Point – located in Essex, Maryland, this 1971 golf course is a more challenging course. Enjoy the picturesque views from the only waterfront golf course on the Chesapeake Bay.
  • Back Creek Golf Course – located in Middletown, Delaware, this links-style course has been awarded as one of the “Best 100 Modern Courses in the US.”
  • Links at St. Anne’s – also located in Middletown, Delaware, this links-style course is great for beginners as you won’t hit into other golfers. They have a wonderful restaurant, sure to provide a great time.
Rock Hall Fishing Charters - Captains Fishing

*Photo from Rock Hall Fishing Charters

4. Try to Catch the Big One with Rock Hall Fishing Charters

Owned and led by Captain Mark Hall, a local born and raised, his passion for fishing is unmatched. Captain Mark has recruited the best Captains on the Eastern Shore, and together they guarantee an incredible fishing adventure. Whether it is fishing for bass or hunting waterfowl, you are sure to have a great time on the Chesapeake Bay.

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Kayaking in Maryland - Couple at Great Oak Manor

5. Try Your Hand At Kayaking, Paddle Boarding & Canoeing

The Great Oak Manor is an award-winning waterfront bed and breakfast on the Eastern Shore. Steps from the property, guests can try their hand at paddle boarding, canoeing, and kayaking using our complimentary equipment. After your adventures on the water, toast your successes on our deck with a frosty beverage or a glass of wine while enjoying spectacular sunsets.

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Biking in Maryland - Smiling Couple

6. Go Cruisin’ on a Bike

Grab a complimentary cruiser bike from Great Oak Manor and hit a trail or the road with your loved ones. Guests love the beauty of the area and we have the Maryland Bike Map you can use as a guide for your adventures on two wheels.

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Antique Store Shopping in MD - Old Book

7. Hunt For Some Hidden Gems in our Antique Shops in Kent County

Kent County is an antique lovers dream with 9 different shops to enjoy featuring historical gems from the past. Roll up your sleeves and get ready to enjoy some incredible shopping and a glimpse into a life that once was.

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Walking tours in Chestertown, MD - Couple Holding Hands

8. Chestertown History Walks Are a Must

History buffs unite with walking tours of Chestertown, Maryland. The tour showcases what life was like before the Revolutionary War. The tour ends with tea at the White Swan.

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Theater in Maryland - Live Play

**Photo by Garfield Center for the Arts – Jeff Weber

9. Attend a Play or Musical Program at the Theatre

Treat yourself to the arts with a wonderful musical, play or concert at two incredible facilities. Check out their websites to find out if there is a production while you are in town.

  • Garfield Center for the Arts – located in Chestertown, MD, you can view their calendar of events and purchase tickets right on their website. Enjoy Annie The Musical, Where the Wild Things Are and much more!
  • Church Hill Theatre –  located in Church Hill, Maryland, they produce some big name shows like Jesus Christ Superstar by Andrew Lloyd Webber. Check out their calendar on their website for upcoming events and shows.
Eastern Shore B&B - Room

10. Unwind In a Stunning Room or Suite

Our 12,000 square-foot Georgian-style estate located waterfront on the Chesapeake Bay offers 13 stunning and romantic guest rooms, wonderful breakfast and incredible sunsets. Take advantage of our seasonal VIP specials and packages and enjoy a memorable escape from the ordinary at Great Oak Manor.

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