HH Ranch on Smith Island

HH Ranch on Smith Island Vacation rental property on Smith Island on the Chesapeake Bay in Maryland

09/01/2026

It was a great day on Smith Island today. Say hello to our new stand up paddle board. We now have two! I took it out for a spin and it did well. And I didn’t fall in. Not bad for a kayaker 😆. So now when you visit the HH Ranch you can enjoy the use of our 2 kayaks (12’ and 16’) 2 inflatable stand up paddle boards (each 11’) and two bicycles. Oh and of course the mean green machine our golf cart!! Plenty of ways to see the island. It’s still beautiful out here and we are open year round!

06/28/2026
Recorded right here at the house
06/10/2026

Recorded right here at the house

Jerry Smith is a waterman, history buff, YouTube creator, and life-long resident of Smith Island in the Chesapeake Bay. If he looks familiar, you probably saw him in Peter Santenello's viral video about the island in 2024, which has been viewed 5.2 MILLION times and resulted in a GoFundMe raising more than $38,000 to repair Jerry's hurricane-damaged house. Chris and Crystal hung out with Jerry in the village of Ewell on Smith Island, which is accessible only by boat.

Topics discussed:

● How Jerry got hooked up with the world-famous vlogger-journalist Peter Santenello two years ago.

● Spending a day with Peter, the viral video, and the surge of interest in Jerry and his content after it came out.

● Jerry's nickname, the Rogue's Point Pirate, inspired by the earlier name for Rhodes Point and his pirate ancestor Marmaduke Mister.

● Early Smith Island settlers (and Jerry's ancestors) of the mid-1600s.

● Chris's and Jerry's shared appreciation for Paul Baker Touart's book Somerset: An Architectural History.

● Authors who have written about Smith Island, including Frances Dize and Tom Horton.

● Life on the island in the 60s and 70s; dressing up to go to Crisfield; businesses closed on Sundays.

● Old Bay vs. J.O. Spice? (Jerry's answer may surprise you!)

● Jerry's crabcake recipe, plus a recipe for a lesser-known dish, "stewed jimmies." 🦀

● Challenges in the crabbing industry, and the significant barriers to entry for young people.

● Tourism and recent come-heres on the island, and Jerry's optimism about the future.

👇 Spotify link in comments! Also available on most streaming platforms including Apple, iHeart, and Amazon.

06/10/2026

Check out this fantastic video by our guests that stayed with us last weekend.

05/27/2026

Check out our friendly neighbor Magellan when you visit the HH Ranch! He’s so cute and friendly

It’s almost Memorial Day which means everything is open on Smith Island. The HH Ranch is ready to host you now and all y...
05/18/2026

It’s almost Memorial Day which means everything is open on Smith Island. The HH Ranch is ready to host you now and all year. The summer is a busy time on the island so be sure to pay us a visit. We’ve got kayaks, bikes and a golf cart for you to explore the island and all its beauty. Check us out at www.kayaksmithisland.com.

Address

20916 Caleb Jones Road
Ewell, MD
21824

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