I’ve driven through the Eastern Shore of Virginia countless times en route to points north. Rolling past roadside farm stands, historic rural churches and one stoplight towns I’d mentally note that one day I needed to stop and check things out but, as with many things in life, my attention and time were pulled elsewhere. Connected to the rest of Virginia only by the 20 mile long Chesapeake Bay Bridge Tunnel, the Eastern Shore is a rural area that’s retained much of its own culture heavily influenced by the farmers and watermen that have called this area home for centuries. Vacationers flock to the the tourist heavy beach resorts of Ocean City, Maryland to the north and Virginia Beach to the south leaving the charms of the Eastern Shore a relatively untouched secret. After hearing of the natural beauty and relaxed way of life from a good friend I resolved to start exploring these secrets for myself.
Sandwiched between the Atlantic Ocean to the east and the Chesapeake Bay to the west, the Eastern Shore has miles of inlets and waterways just perfect for exploring by kayak and a new wave of vineyards looking to take advantage of the mild climate and fertile soil. Southeast Expeditions leads a popular “Paddle your Glass Off” tour which highlights the natural beauty of the Eastern Shore along with a visit to Chatham Vineyards to sample some of their vintages.
Kayaking and wine? I was in.
We arrived in the sleepy fishing village of Bayford as the oystermen finished bringing in their morning haul with a friendly yellow lab serving as the town’s official welcoming committee. Our guide Ethan was already waiting for us with all the equipment we’d need for the day’s adventure. After a quick safety briefing and paddle demo it was time to head out on the water.
A leisurely hour long paddle wound its way along the still waters of Nassawadox and Church Creeks, some of the many inlets branching off from the Chesapeake Bay. The calm water is perfect for a novice kayaker with the only obstacles to navigate being the odd crab pot buoy or (if your friends paddle as well as mine do) an errant kayaker here and there. Much of the Eastern Shore is protected for conservation so you won’t see a lot of development along its waterfront.
What will you see?
Peaceful blue water,coastal oaks and pines and an array of wildlife are all part of the longest stretch of wild shoreline on the East Coast. Ethan gave us a thorough overview of the area which has a rich history spanning over 400 years while pointing out osprey and blue heron along the treeline.
As we pulled into shore we were treated to a view of a beautifully restored federalist style home. While the home was originally built in 1818 ( and served as a medical facility during the Civil War), the land here has been farmed since the 1600’s making it one of the oldest continuously run farms in the United States. The land’s current owners John Wehner, a second generation wine-grower, and his wife Mills started Chatham Vineyard in 1999. As we walked along the vines towards the tasting room, the couple (both of whom look like they stepped from the pages of a J.Crew catalog) warmly greeted our group as they went about setting up for a charity oyster roast to be held later that evening.
The high-density, European-style vineyards feature Chardonnay, Merlot, Cabernet Franc, Cabernet Sauvignon and Petit Verdot grapes that are used to make the Estate’s signature wines. The tasting started with the Vineyard’s award-winning Chardonnays then followed a natural progression of rosè and red before ending with a dessert wine. As part of the tour I was able to select a bottle to either enjoy on site or take home. I choose the peppery Cabernet Franc to enjoy with my friends on this gorgeous, sunny afternoon.
Just for good measure, I thought it was a great idea to order a cheese plate since we still had to paddle back.
Light winds and an outgoing tide made our return trip a breeze. Ethan joked that most people actually paddle a bit better after the wine tasting since they’re more relaxed. While I don’t know if I was paddling any better I was certainly more relaxed myself. Now that I’ve gotten a taste of the Eastern Shore’s charms I know I’ll definitely be back.
Want to paddle your glass off?
Contact Southeast Expeditions to set up your own kayak winery tour. They also offer a variety of other tours, classes and rentals to help you best enjoy the natural setting of the Eastern Shore.
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Katrina says
I love the “paddle your glass off” title of the tour! Now I really want to go on it!
Marie says
We’re from Florida and miss home often. Thanks for bringing us back a little! It’s easy, once you start traveling the world, to forget jut how beautiful your own back yard is!
Sammi Wanderlustin' says
That looks like a lot of fun- it’s like you’re working off the wine before you’v even started haha! What a great idea 🙂
Brianna says
Paddling after the wine wasn’t as bad as I thought either!
Mindi @ 2foodtrippers says
It’s smart that you got the cheese plate for extra energy for the way back. Looks like fun!
Brianna says
I am definitely a cheap date when it comes to alcohol, I definitely needed some extra fuel to get me back!
SouthEast Expeditions says
Glad to have you and your gang, Brianna! What a gorgeous day that was! Thank you for visiting and writing us up in your lovely blog here. For anyone who’s thinking of joining us for a paddle this fall, we run trips daily well into November (and by appointment even later)! See you on the water!
Thanks,
Margaret
SouthEast Expeditions
Brianna says
Thank you so much for having me Margaret, I’ll definitely be back to explore more of the Shore.
SJ @ Chasing the Donkey says
Now you have a brilliant idea! What better way to get me of the couch, than with wine! Awesome.
Brianna says
Wine is a great motivator isn’t it?
Susan says
One thing I love about the east coast is not only is it beautiful, but that it is rich in so much cultural history. What a great way to spend the afternoon in Virginia, kayaking then wining!
Brianna says
It was a fantastic way to spend a beautiful day 🙂
Michael Huxley says
Who’d have thought kayaking and wine would go so well together? At least it wasn’t the other way around! ;D Sounds like a fantastic day out though. Loving your blog, keep up the good work!
Brianna says
Thanks so much Mike 🙂 I’m sure if I had done the wine first I’d have much more interesting pictures lol
Sandra @ Tripper says
The strangest yet most delicious combination ever: kayaking and wine 🙂 Love these posts about less “popular” areas.
Brianna says
I find off the radar places tend to have more charm
Fie says
Looks like a nice day out…
Brianna says
It was an awesome way to spend an afternoon.
James RK says
Great idea for a wine tour, might have to research if something is similar in my city as it seems like a great way to spend a day.
Duke Stewart says
Such a fun-looking tour, mixing up two of my favorite things. I truly hope that tour stays around for a while because I’ll definitely want to Kayak and have some wine when I get back in the area. Thanks for sharing this!
Bente Vold Klausen says
Wine and kayaking is a creative combination. But I love the calmness of traveling on the water. Your pictures give a good impression of what this day can offer.
coffee in a cup says
love the idea of a kayak winery tour! but then again, i love anything that involves wine 😉
Heather Cole says
Love this, two of my most favourite things at once, must try and get it introduced here in the Lakes (though not sure we’re know for our wine production). We do have ospreys and herons though, so perhaps we’re half way there. Looks like so much fun!
Brianna says
Perhaps kayak and ales?
Vicky says
A wine and kayaking tour…amazing! The house on the vineyards looks absolutely stunning, and good shout on the cheese plate – sounds like my perfect day!
Brianna says
It really was a perfect day.
elaine schoch says
Looks like a fun way to spend the day checking out a new area and exploring different wines. Love it!
Brianna says
What’s not to like?
Adelina // Pack Me To says
Kayaking and wine. Sounds like a lot of fun! I’d definitely do it.
Brianna says
You definitely should!
Adrian of Adrian's Travel Tales says
Kayaking and wine seems to go well with my other friend, hiking and beer. I think I’ll definitely be trying this out! 😀 Thanks for the idea.
Brianna says
Another classic combo!
Elena says
Kayaking and wine! What a great combination! When we go kayaking we usually get beers but wine doesn´t sound bad either 🙂
Brianna says
I’m going to try paddleboard and bourbon next lol
Natasha says
Wow wine & water the paddle back is definitely going to be the most challenging ….
Brianna says
It actually wasn’t too bad
samiya selim says
Sounds like a fun combination! kayaking and wine tasting, love them both:-)
Brianna says
Me too, I can’t wait to go back.
Hannah says
Kayaking and wine? Hello! Win win for sure!
Brianna says
What’s not to like?
Katie @ Domestiphobia says
That seriously looks like the perfect day!
Brianna says
You should definitely head out there, you’d love it!
Michelle says
I love VA’s Eastern Shore. It’s so peaceful. I’ve done bike tours to wineries, but I’ve never done a kayak tour to a winery. It sounds like fun.
Brianna says
It made for a perfect day and I can’t wait to return to the Eatsern Shore.
San says
Oh I miss kayaking! Looks like loads of fun in a great area 🙂
Brianna says
It was great fun, sounds like its time for you to get back out on the water!
Amy says
This looks like so much fun! I used to live in Northern Virginia and would daytrip to the coast every once in a while. It’s such a gorgeous area. Wish I knew about this tour then, but I guess it’s just another reason to go back!
Carmen (CarmensTravelTips) says
Kayaks and wine what a great combination. What a fun day. Thanks for linking up to #WeekendWanderlust.
Corinne says
Kayaking then wine…kayaking with wine…all looks and sounds good to me.
Brianna says
Me too!
alexa says
First, congrats on all the comments. Awesome! Like to know your secret. Love kayaking. Really fun article!
Brianna says
Thanks so much for stopping by! A day with wine and kayaking is bound to be a good one.
Megsy says
Kayaking and wine – what an awesome way to spend a nice day out with friends. I’d love to give this a try!
Brianna says
It was such a fun day, I highly recommend it!
Melvin says
What a beautiful place! That should be great for kayaking, right? I will definitely come there to enjoy. Thanks for great information and photos.
Brianna says
The Eastern Shore is just perfect for kayaking you should definitely come by for a visit!