The Chesapeake Inn

10/08/2026

The weather is looking perfect on Saturday for the Urbanna W**e & Oyster Stroll 2026 ! 17 w**e tastings and 3 oyster tastings, shopping and snacking at 15 participating shops and restaurants. Stay safe and make a night of it - book a room while we still have rooms available for Saturday night!! (And you can order tickets while you book your room!)

From 2 to 5pm, take a leisurely stroll along the charming streets of Urbanna and enjoy tasting samples of w**e, fresh oysters, and other tasty morsels at participating restaurants and shops.

10/04/2026

We love hosting the little Miss Spats!

10/02/2026

Join us and Let’s Maj RVA for our first ever mahjong retreat!! Come for the weekend or just one night - it will be a fabulous time!

I know. It’s Halloween weekend.

And if you still have little ones at home waiting to put on costumes and fill their buckets with candy, this probably isn’t your weekend.

But maybe your little ones aren’t so little anymore.

Maybe Halloween looks different these days.

Maybe you’ve reached that season where you can leave for a night or two—but you’re so used to being the one who stays home, takes care of everyone, makes the plans, cooks the meals and keeps everything moving that you almost forget you’re allowed to go.

So consider this your invitation.

Come to Urbanna.

Let someone else take care of the meals. Play mahjong. Stay up laughing. Shop a little. Sleep in. Sit around the table longer than you normally would. Meet women you didn’t know before and leave knowing them.

And if you’re thinking, But I don’t have anyone to go with…

Come anyway. You won’t be the only one.

If two nights away feels like too much, come for one.

We intentionally kept this retreat small, and there are just a few overnight spots left.

Sometimes you don’t need a big vacation or a reason.

Sometimes you just need to go.

And there’s a seat waiting for you.

October 30–November 1 | Urbanna
One- and two-night options available. Link in bio.

09/28/2026

It's finally fall and oysters are at their very best! We're sold out for the Urbanna Oyster Festival but here's a local secret . . . the Urbanna W**e & Oyster Stroll is even more fun! Enjoy delicious w**es, oysters and other delectables at 14 different locations across town -- book a stay and reserve your tickets while you can!

09/24/2026

Incredible! Had the honor of hosting a real live descendent of a Signer of the Declaration of the Independence at The Chesapeake Inn last night! Luther Shank IV can trace his lineage to John Hart of NJ, a Revolutionary War hero. Thanks for sharing some magic with us at the inn, Luther!

09/24/2026

Thank you to the Virginia CEOs for choosing The Chesapeake Inn for your private round table venue last week! We were thrilled to host you. Our Lobby/Living Room, Rappahannock Room, Game Room and other beautiful, functional meeting spaces - not to mention our 12 gorgeous guest rooms and famous personalized hospitality - make the inn the perfect place to hold your leadership meeting, office retreat, or small group getaway!

09/17/2026

Life leave you feeling a little witchy? The best cure for the crankiness is to make a plan to let your inner witchiness OUT! Grab your best witchie buddy for the 23rd … it will be a night to remember! (And feel free to bring your black cat because we’re pet friendly!)

PS we normally have a two night minimum but if you’re riding the waves with Main Street we are happy to waive that requirement for you! Make sure to let us know you’re participating - we’ll save one of our kayaks for you!

Witches, unite! 🧙‍♀️🌊 The first annual Urbanna Witches Paddle is officially here, and Urbanna Creek is about to look a little... enchanted.

Grab your kayak, canoe, or paddleboard, put on your witchiest attire (and your lifejacket!), and join us for a paddle around Rosegill Beach. Launch from the town marina or wherever you have access, we'll all meet back at the marina for a group photo.

Can't paddle? No problem! You are still more than welcome to dress up and come to the marina for the photo. The more witches the better. 🖤

After the paddle, walk up the hill with us for a little witching hour, aka a post-paddle happy hour at Urbanna Pearl Oyster Tavern. 🍹🕯️

Registration is required and we are asking for a $25 donation to Urbanna Main Street.

https://www.eventbrite.com/e/urbanna-witches-paddle-tickets-1999386483795

See you on the water, witches!

P.s. would anyone want a commemorative t-shirt or sweatshirt? 🧙🏼‍♀️

09/07/2026

So many great events in Urbanna this fall!

09/05/2026

One of our very favorite events in Urbanna! Kick of the holiday season with small town charm - in addition to the Urbanna Holiday Home Tour, the first weekend in December includes a Christmas Parade, a fashion show, a tree lighting ceremony and fabulous shopping!

Save the date! 🎄 Urbanna's Holiday Home Tour is back.

Saturday, December 5th, 2026, 11-4pm.

More details to come.

09/01/2026

Yay for September!! There are SO many exciting things happening in Urbanna this fall! And add to this list the live music most of our restaurants offer!