Five Fun Things to do in Urbanna, VA

Exotic and faraway destinations are great, but sometimes it’s just as much fun to play in your own backyard. One of our favorite things about living in D.C. was the easy access to dozens of weekend getaways, from the mountains to the shore and so much in between. We spent a fun Fall weekend on the Chesapeake Bay in Virginia, a quick two hour drive from home.

We drove all over the Northern Neck, but our base was in Urbanna, a tiny town with big personality. Although mostly famous for its annual oyster festival, we discovered that there are plenty things to do in Urbanna all year round.

The Urbanna Walking Tour

Urbanna has a lot of historical significance, which is showcased through a self-guided walking tour of the town’s notable landmarks. We didn’t do the whole thing, as it was rather cold on Sunday morning. But we had lots of fun rambling through a few of the stops.
Located right across from our hotel, Lansdowne, a lovely Georgian-style house where Arthur Lee once lived, was our first stop. The house is now a private residence, but tourists are still able to peep the architecture through a picturesque picket fence in front of the property, which is estimated to have been built as early as 1750.

Up next was the former courthouse, which has now been converted into a church. According to the walking tour’s website, it was built in 1748 and is one of only eleven colonial courthouses still standing in Virginia today.

Next door, we marveled at the Gressitt House, which is believed to be the oldest home in Urbanna dating back to the 1740s. The house, with its adorable front porch that begs for a glass of lemonade and leisurely chats, still has its original flooring in tact. I was tempted to knock on the door for a tour.

Catch a Bay Breeze

In Urbanna, you’re never that far from the water. Fall may not be the best time to jump in, but the views are just as nice from the shore.

Have a Proper Meal

Of course, you should order the local oysters as often as possible, but don’t stop there. For dinner, try The Works Bar & Grill, an upscale sports bar with a diverse food menu and live music on the weekends. The Works also celebrates another fun piece of Urbanna history, a Coca Cola bottling plant that operated throughout the 1920s and into the 1960s. The restaurant is decorated with Coke memorabilia throughout, for a cool retro vibe.
We had a great dinner here. The dining room seemed filled more with locals than tourists, probably due to the time of year, and the live music was great. We shared a massive prime rib and a plate of delicious calamari with a Thai chili sauce.
For breakfast, head right across the street to Something Different, a full service restaurant and market “specializing in fine neanderthal cuisine”. This restaurant is fun from start to finish. Again, capitalizing on town history, the tables are made from stable doors of an old farm and race track nearby. They also roast their own coffee beans and serve some truly delicious coffee.
There is nothing better than a no-frills breakfast in a small town, and this was no exception. Tom and I both ordered the bbq omelet, stuffed with tender pulled pork, cheddar cheese and house made Shindig sauce.
We were both obsessed with this meal, and ended up buying two bottles of bbq sauce from the market, the Shindig which is a tomato based sauce with lots of tang and a Carolina vinegar sauce that I’ll be putting on pretty much everything I eat until it runs out.

Feel Like a Kid Again at Mini Golf

Urbanna is home to one of the cutest and better maintained mini golf courses I’ve been to in ages. Tom will never pass up the chance to do anything golf related, so this was a must for us. Take your kids or just channel your inner child for an hour or so of throwback fun.

Get a Good Night’s Rest at the Chesapeake Inn

The highlight of our stay may actually have been our adorable and comfortable stay at The Chesapeake Inn. The decor is colorful and quirky, which I loved, with lots of nods to the nautical.


The staff was incredibly pleasant as well, making for a wonderful experience from start to finish. The rooms offer private baths, full size refrigerators and microwaves. It’s a great place for a quick getaway or a much longer stay. Our trip was much shorter than I would have liked. But in just two short days Urbanna stole a piece of my heart and I think it will yours too!

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