Revving Up to the Weekend: Live Music at Jamestown Settlement This February
By John Womeldorf | February 2026
If you’ve followed me for any length of time, you know this already: I’m a huge music fan. From tiny listening rooms to packed outdoor shows, I’m always on the lookout for interesting venues and great live performances.
So when I saw that Jamestown Settlement is hosting a Thursday Evening Music Series this February, my ears immediately perked up.
Three Thursdays. Three outstanding artists. A waterfront historic setting. Art exhibits. A cash bar. And live music at 6:30 p.m.
Yes, please. 🙌
The “Revving Up to the Weekend” series runs on February 12, 19, and 26, 2026, and it’s part of Jamestown Settlement’s annual Black Artist Showcase. It’s a chance to enjoy music, connect with friends, and experience one of Williamsburg’s most unique venues in a totally different way.
🎤 Sammy Lee — February 12 at 6:30 p.m.
The series kicks off with Sammy Lee, and he’s bringing some serious soul with him.
Rooted in the blues, Sammy blends acoustic folk, Motown influences, and raw emotional storytelling into something that’s truly his own. His baritone voice is powerful, gritty, and honest—and the kind that makes you stop mid-conversation and say, “Wait… listen to this.”
With more than a decade of performance experience, he knows how to work a room. Expect a soulful, high-energy, and deeply personal set.
If you love blues, roots music, and great songwriting, don’t miss this one.
🎶 Roberta Lea — February 19 at 6:30 p.m.
On February 19, the stage belongs to Roberta Lea—an award-winning singer/songwriter with a sound she describes as “country-neo-pop with a delicious, folky flair.”
She’s a touring member of The Black Opry, part of CMT’s Next Women of Country Class of 2023, and a voting member of The Recording Academy.
Translation? She’s the real deal.
Her music comfortably moves between Country, Folk, and Americana, and she has that rare ability to connect with just about any audience. Whether you’re a longtime country fan or more of an indie-folk listener, you’ll find something to love here.
✨ Akeylah Simone — February 26 at 6:30 p.m.
The series wraps up on February 26 with Akeylah Simone, and this one promises to be something special.
Akeylah is one of those artists who refuses to be boxed into a single genre. Neo-Soul. R&B. Pop. Jazz. Rock. She moves between them effortlessly—and always with style.
She’s based right here in Hampton Roads, and her performances are known for being uplifting, soulful, and deeply engaging. You may not know exactly what she’s going to play next—but you can be sure you’ll leave feeling better than when you arrived.
And honestly, that’s my favorite kind of show.
🎟️ Tickets & Details
Here’s the good news: this is one of the best entertainment values you’ll find all winter.
- $15 for Adults (13+)
- $10 for Students (with valid ID)
- All shows start at 6:30 p.m.
- Location: Jamestown Settlement
You get great music, a beautiful setting, access to the Black Artist Showcase, and a relaxed social atmosphere—all in one evening.
Why I Love This Series
What makes this series so appealing to me isn’t just the talent (though it’s excellent). It’s the setting.
Listening to live music at Jamestown Settlement—right on the James River, surrounded by history—is about as “Williamsburg” as it gets. It’s familiar, yet totally different from your typical concert venue.
It’s perfect for:
- Date nights
- Meeting friends after work
- A low-key night out
- Anyone who loves discovering new artists
If you’re looking for something fun, local, and a little outside the box this February, this checks all the boxes.
I’ll probably be at one (or all) of these. If you see me, say hello. 🎶
Meet Your Local Guide: Mr. Williamsburg
Pssst! I’m going to let you in on a little secret… While I am a real estate agent, I’m not your average one.
I’ve built my reputation on being a local ambassador first and a Realtor second. Known throughout the region as Mr. Williamsburg, I’ve made it my mission to help people fall in love not just with a house, but with the lifestyle of Greater Williamsburg, Richmond, and Hampton Roads.
Looking to sell your home in Williamsburg (or anywhere nearby)? I take a storytelling approach that goes beyond square footage and granite countertops. I’ll help you showcase your home’s unique story — one that future buyers can connect with on a personal level.
👉 “Every Home Has a Story”: https://mrwilliamsburg.com/mr-williamsburg-home-stories/
👉 Market Value: https://mrwilliamsburg.com/contact
👉 Testimonials: https://mrwilliamsburg.com/testimonials/
📞 Call/Text: (757) 254-8136
✉️ Email: John@MrWilliamsburg.com
🌐 Website: https://mrwilliamsburg.com
Your real estate journey should feel like your journey — not a transaction. I’ll meet you where you are and help you navigate what’s next.
Warmly,
John Womeldorf
A.K.A. Mr. Williamsburg