Spring in historic Downtown Ashland, Virginia
🌸 MAY 1–9 — Spring Spectacular at Randolph-Macon College
Spring in Ashland just feels different, doesn’t it? The trees are showing off, the air is a little softer, and right in the middle of it all, the show choir at Randolph-Macon College is ready to take the stage.
Their Spring Spectacular is one of those performances that wraps you up in joy from the very first note — full of energy, talent, and the kind of hometown pride that reminds you why we love it here so much.
If you’ve been craving a night out that feels uplifting, easy, and just plain fun… this is your sign.
📅 May 1–9, 2026
📍 Blackwell Auditorium, 205 Henry St, Ashland, VA 23005
🔗 https://www.rmc.edu/campus-life/arts-and-events/
🌿 MAY 2 (9 AM–12 PM) — Ashland Farmers Market Opening Day
There is nothing like that first Saturday back at the Ashland Farmers Market.
The tents go up, the music starts drifting through the air, and suddenly you’re holding fresh flowers in one hand and a warm baked good in the other, wondering why you don’t do this every week (spoiler: now you can).
This is your chance to shop local, eat fresh, and reconnect with the people who grow and make the things we love. Come early, stay awhile, and soak up every bit of it.
📅 Saturday, May 2, 2026
⏰ 9:00 AM – 12:00 PM
📍 Ashland Farmers Market, 121 Thompson St, Ashland, VA 23005
🔗 https://www.ashlandva.gov/287/Ashland-Farmers-Market
🎨 MAY 2 (10 AM–1 PM) — Plein Air Painting Day
If you’ve been needing a creative reset, this is a gentle nudge to step outside and try something new.
Out on the grounds of the Hanover Arts and Activities Center, artists of all levels are gathering to paint in the open air — no pressure, just fresh perspective and a little inspiration from spring itself.
It’s peaceful, it’s playful, and honestly… it’s kind of magical to see what happens when you slow down long enough to notice what’s around you.
📅 Saturday, May 2, 2026
⏰ 10:00 AM – 1:00 PM
📍 Hanover Arts and Activities Center, 500 S Center St, Ashland, VA 23005
🔗 hanoverarts.net
🐎 MAY 2 (4–7 PM) — Derby Party at Center of the Universe Brewing
Mark your calendar and start planning your outfit now — because Derby Day at Center of the Universe Brewing Company is always a moment.
We’re talking big hats, live music, mint juleps, raffles, and a whole crowd of folks ready to celebrate together. Whether you’re there for the race, the style, or just a really good afternoon with friends… you’re going to have a great time.
📅 Saturday, May 2, 2026
⏰ 4:00 – 7:00 PM
📍 Center of the Universe Brewing Co, 11293 Air Park Rd, Ashland, VA 23005
🔗 https://www.facebook.com/events/1611607516695114
🐎 MAY 2 — Derby Day at Thompson Street Tavern
If your perfect Derby Day looks a little more cozy and a little more “let’s grab a table and stay awhile,” then Thompson Street Tavern has you covered.
Bring your people, order your favorites, and settle in for all the excitement of race day — no stress, just good food and good company.
📅 Saturday, May 2, 2026
📍 Thompson Street Tavern, 125 Thompson St, Ashland, VA 23005
🔗 https://thompsonsttavern.com/
🧘♀️ MAY 4 (10:30 AM) — The Exhale Series
You know that feeling when you didn’t realize how much you needed to slow down… until you finally do?
That’s exactly what The Exhale Series at the Hanover Arts and Activities Center offers. Through immersive sound and guided breathwork, this experience helps you release tension and reset — mind, body, and spirit.
All you have to do is show up, lie back, and let yourself rest.
📅 Monday, May 4, 2026
⏰ 10:30 AM
📍 Hanover Arts and Activities Center, 500 S Center St, Ashland, VA 23005
🔗 hanoverarts.org
🏆 MAY 4–17 — Heart of Hanover Awards Voting
This is one of the easiest (and most meaningful) ways to show some love to the businesses that make our community shine.
From your favorite coffee spot to the shop that always remembers your name, the Heart of Hanover Awards are all about celebrating the places and people who make Ashland feel like home.
Take a few minutes, cast your votes, and cheer on your favorites 💛
📅 Voting open May 4–17, 2026
🔗 https://www.hanovervirginia.com/start-and-grow-your-business/hanover-legacy-companies/
🌱 MAY 5 (6 PM) — Open Mic Night
There’s something really special about a room full of people cheering each other on — and that’s exactly what Open Mic Night at Center of the Universe Brewing Company feels like.
Whether you’re performing or just soaking it all in, it’s a night of connection, creativity, and a little bit of courage. You never know who you’ll hear… or what moment might stick with you.
📅 Tuesday, May 5, 2026
⏰ 6:00 PM
📍 Center of the Universe Brewing Co, 11293 Air Park Rd, Ashland, VA 23005
🔗 https://tinyurl.com/5bj5zfeu
🌍 MAY 5 — Export Compliance Webinar
If you’re a small business owner with big dreams, this free webinar is a quiet powerhouse of an opportunity.
Learn how to navigate international trade with confidence and open doors you may not have even considered yet. Growth starts with knowledge — and this is a great place to begin.
📅 Tuesday, May 5, 2026
🔗 https://exportvirginia.org/services/training
🌱 MAY 6 (6–7:30 PM) — Entrepreneur Bootcamp
Got an idea that won’t leave you alone? The Downtown Ashland Association’s Entrepreneur Bootcamp is where those ideas start to take shape.
Hosted at the Ashland Branch Library, these sessions are welcoming, practical, and full of the kind of support every entrepreneur needs.
Come as you are. Leave with clarity, connection, and a little more confidence.
📅 Wednesday, May 6, 2026
⏰ 6:00 – 7:30 PM
📍 Ashland Branch Library Conference Room, 201 S Railroad Ave, Ashland, VA 23005
🔗 ashlandvirginia.com/bootcampom/bootcamp
🎤 MAY 7 (6–8 PM) — Pitch Competition at the Ashland Theatre
This is one of those nights where you can feel the energy in the room.
At the Ashland Theatre, local entrepreneurs take the stage to pitch their ideas, share their passion, and compete for a chance to win funding to bring their visions to life.
It’s exciting, inspiring, and a beautiful reminder of how much creativity lives right here in our community.
📅 Thursday, May 7, 2026
⏰ 6:00 – 8:00 PM
📍 Ashland Theatre, 205 England St, Ashland, VA 23005
🔗 https://www.ashlandvirginia.com/pitch
🌸 MAY 7 — Mother’s Day Flower Preorders Close
If you’ve ever wanted to give a gift that feels truly thoughtful, this is it.
These farm-grown blooms are designed right here in Ashland — seasonal, intentional, and absolutely beautiful. Preorders close soon, so don’t wait too long to claim yours.
📅 Preorders close May 7, 2026
📍 Pickup across Ashland, Mechanicsville & Richmond (May 9–10)
🔗 https://www.breemarflowerfarm.com/mothers-day-flower-collection
🎬 STARTING MAY 8 — The Sheep Detectives
Looking for something a little different (and a lot of fun)? Head to the Ashland Theatre for The Sheep Detectives — a quirky, clever mystery that’s equal parts charming and entertaining.
It’s the kind of night out that feels easy and unexpected in the best way.
📅 Opens Friday, May 8, 2026
📍 Ashland Theatre, 205 England St, Ashland, VA 23005
🔗 https://www.ashlandtheatre.org/
🌿 MAY 9 — Hanover Master Gardeners Plant Sale
If you’ve been dreaming about your garden — or even just thinking, “maybe this is the year I finally figure out plants…” — this is your moment.
The Hanover Master Gardeners Plant Sale is one of those feel-good, community-rooted events where you can browse beautiful, locally grown plants and get real advice from people who genuinely want to help you succeed.
From herbs and vegetables to native plants and those famous Hanover tomatoes, it’s all here — along with a few surprises (including some fun Mother’s Day activities for the kids).
Come curious, leave inspired… and maybe with a car full of plants 🌱
📅 Saturday, May 9, 2026
⏰ 9:00 AM – 1:00 PM
📍 13015 Taylor Complex Ln, Ashland, VA 23005
🔗 https://hanovermastergardeners.org/hanover-master-gardeners-plant-sale/
🛍️ MAY 9 — England Street Spring Market
There’s something so special about wandering a market where everything is handmade, thoughtfully curated, and created by people right here in our community.
The England Street Spring Market is exactly that kind of experience — relaxed, welcoming, and full of treasures you didn’t know you needed until you saw them.
Hosted by Thrill of the Hunt, this outdoor market brings together local makers and artists in a space that feels equal parts shopping trip and Saturday stroll.
Take your time, meet the vendors, and enjoy one of Ashland’s sweetest little traditions.
📅 Saturday, May 9, 2026
⏰ 11:00 AM – 4:00 PM
📍 315 England St, Ashland, VA 23005
🔗 https://www.thrillofthehuntva.com/market
🎶 MAY 9 — Bald Tomorrow Music Festival & Fundraiser
This is more than just a day of live music — it’s a day that means something.
At Center of the Universe Brewing Company, the Bald Tomorrow Festival brings together incredible bands, food trucks, and a whole lot of heart to support childhood cancer research.
You’ll find yourself singing along, running into friends, and feeling that unmistakable sense of community — all while supporting a cause that truly matters.
It’s joyful, it’s meaningful, and it’s one of those events that reminds you how powerful showing up can be 💛
📅 Saturday, May 9, 2026
⏰ 1:00 – 8:00 PM
📍 Center of the Universe Brewing Co, 11293 Air Park Rd, Ashland, VA 23005
🔗 https://www.facebook.com/events/1608895813703083
🌿 MAY 9 — Camptown Races Remembered
If you’re looking for an evening that feels a little more elevated — a little more “this is something special” — this is it.
Set against the beautiful backdrop of Eagle Point Farm, Camptown Races Remembered is an experience filled with music, great food, signature drinks, and meaningful moments.
You’ll have the chance to explore behind the scenes, enjoy live entertainment, and even take part in auctions featuring unique pieces of history — all while celebrating a tradition that has deep roots in our community.
It’s elegant, it’s memorable, and it’s the perfect way to close out a full day in Ashland.
📅 Saturday, May 9, 2026
⏰ 5:00 – 8:00 PM
📍 Eagle Point Farm, Ashland, VA
🔗 https://checkout.square.site/merchant/72Y88MXBQ0YGP/checkout/WJIYQ4PMGTUARWRIYFRG7X3D
💐 MAY 10 — Mother’s Day at Center of the Universe
If you’re looking for something relaxed, fun, and just a little bit different for Mother’s Day, this is such a sweet option.
At Center of the Universe Brewing Company, the day is filled with mimosas, bingo, flowers, and even mini chair massages for mom. It’s low-key, joyful, and perfect for celebrating in a way that actually feels good.
📅 Sunday, May 10, 2026
⏰ 12:00 – 8:00 PM
📍 Center of the Universe Brewing Co: 11293 Air Park Rd, Ashland, VA 23005
🔗 https://www.facebook.com/events/1964535854188401
🗣️ MAY 12 — Community Input Session
If you’ve ever said, “I wish I could have a say in how things grow around here…” — this is your moment.
Hanover County is inviting neighbors to come share thoughts, ideas, and feedback on future land use planning. It’s casual, it’s informative, and it’s a real chance to help shape what the future of our community looks like.
Because the best version of Ashland? It’s built together.
📅 Tuesday, May 12, 2026
⏰ 3:00 – 5:00 PM
📍 Ashland Branch Library
🥐 MAY 13 — Membership Breakfast
There’s something special about starting your day in a room full of people who care about this community as much as you do.
This monthly breakfast is part networking, part inspiration, and all about connection — with local leaders sharing resources and ideas to help small businesses thrive.
Come for the coffee, stay for the conversation, and leave with something useful (and maybe a new friend or two).
📅 Wednesday, May 13, 2026
⏰ 8:00 AM
📍 RVA Around the Table
🔗 https://map15.wildapricot.org/event-6654933
🎨 MAY 13–JUNE 3 — Fall Into Painting
Midweek just got a whole lot more peaceful.
Each Wednesday evening, artists (and soon-to-be artists) gather at the Hanover Arts and Activities Center to paint, learn, and unwind together. No pressure, no perfection — just a welcoming space to try something new or reconnect with your creativity.
It’s the kind of thing that fills your cup in the quietest, loveliest way.
📅 Wednesdays, May 13 – June 3, 2026
⏰ 6:00 – 8:00 PM
📍 Hanover Arts and Activities Center, 500 S Center St, Ashland, VA 23005
🔗 hanoverarts.net
🧠 MAY 14 — Trivia Night
Alright, this is your chance to prove you do know a little bit about everything.
Trivia Night near the Origin Beer Lab is equal parts competitive and completely lighthearted — the kind of evening where you laugh just as much as you guess.
Bring your smartest friends (or your funniest ones — honestly, both work).
📅 Thursday, May 14, 2026
⏰ 6:00 PM
📍 Origin Beer Lab Beer Garden, 105 Hanover Ave, Ashland, VA 23005
🚗 MAY 16 — KarWanis Car Show
There’s just something about a sunny day, classic cars, and a community that shows up.
The KarWanis Car Show is one of those easy, all-ages events where you can wander, listen to music, grab a bite, and admire everything from vintage rides to modern favorites — all while supporting a mission that gives back to local kids.
It’s simple, it’s fun, and it’s very Ashland.
📅 Saturday, May 16, 2026
⏰ 10:00 AM – 2:00 PM
📍 Ashland Junction Shopping Center, 167 Junction Dr, Ashland, VA 23005
🍽️ MAY 16 — Women in Change Long Lunch
Imagine a table full of incredible women, good food, and conversations that leave you feeling energized and inspired.
That’s exactly what this Long Lunch at the Dominion Energy Innovation Center is all about. It’s relaxed, welcoming, and designed to celebrate and connect women who are making a difference.
Come hungry — for both the food and the inspiration.
📅 Saturday, May 16, 2026
⏰ 1:00 – 3:00 PM
📍 Dominion Energy Innovation Center, Ashland, VA
🔗 https://www.eventbrite.co.uk/e/women-in-change-usa-long-lunch-at-dominion-energy-innovation-center-tickets-1985708956944
🐾 MAY 16 — Patio Pawty
Grab the leash and call your friends — the patio at Center of the Universe Brewing Company is going to be full of wagging tails and good vibes.
With live music, food, and plenty of space for pups and people alike, this is one of those laid-back evenings that just feels like summer is on its way.
📅 Saturday, May 16, 2026
⏰ 4:00 – 7:00 PM
📍 Center of the Universe Brewing Co
11293 Air Park Rd, Ashland, VA 23005
🎶 MAY 16 — Balsam Range Live
If live bluegrass has a way of stopping you in your tracks, you’re going to want to be at the Ashland Theatre for this one.
Balsam Range brings award-winning sound, deep roots, and the kind of performance that reminds you why live music matters. It’s soulful, it’s powerful, and it’s an unforgettable night out.
📅 Saturday, May 16, 2026
⏰ 8:00 PM
📍 Ashland Theatre, 205 England St, Ashland, VA 23005
🔗 https://www.ashlandtheatre.org/
⛳ MAY 18 — The Arc of Hanover Golf Tournament
A morning on the green, a great cause, and a community that shows up for one another.
Whether you’re playing, sponsoring, or volunteering, this tournament supports The Arc of Hanover and the incredible work they do. It’s a meaningful way to spend the day — and a beautiful course to do it on.
📅 Monday, May 18, 2026
⏰ 8:00 AM
📍 Hanover Golf Club
🔗 https://www.thearcofhanover.org/golftournament
🌍 MAY 21 — Getting Paid Webinar
Let’s talk about the part of business that really matters — getting paid.
This free session walks through risk, payment methods, and smart strategies for international business, helping you protect your work and grow with confidence.
📅 Thursday, May 21, 2026
🔗 https://exportvirginia.org/services/training
🎩🌸 Ashland Fourth Fridays - Kentucky Derby Theme
Fourth Fridays is back — and this month, we’re celebrating in style alongside Secretariat for Virginia with a night inspired by the legendary Secretariat.
Think: festive hats, local shopping, live music, and that unmistakable small-town magic we all love.
Start your evening browsing local vendors and handmade goods, grab something tasty from a food truck, and make your way to the parade as Ashland Dance Academy kicks things off with a prancing celebration you won’t want to miss. From there, settle in and enjoy a free live concert by Blue Guitar while the sun sets over Thompson Street.
Be sure to stop by for exclusive Secretariat merchandise, snap a photo with Sign Gypsies of Mechanicsville, and definitely wear your best Derby hat — there’s a Downtown Ashland Association prize on the line, and you know this town does not play around when it comes to hats.
It’s festive, it’s local, and it’s the perfect way to spend a Friday night in the Center of the Universe 💛
📅 Friday, May 22, 2026
⏰ 5:00 – 8:00 PM
📍 Ashland Town Hall, 121 Thompson St, Ashland, VA 23005
🔗 https://www.AshlandFourthFridays.com
🎓 MAY 22 — Randolph-Macon Graduation Celebration
This town loves its students — and graduation weekend is the perfect excuse to celebrate them.
Head over to Il Forno Bar and Grill for music, specials, and a night that feels like one big congratulations.
Because earning that degree? That deserves a party.
📅 Friday, May 22, 2026
⏰ 9:00 PM – 2:00 AM
📍 Il Forno Bar and Grill
🧩 MAY 23 — Puzzle Racing
This one is just plain fun.
Whether you’re competitive or just curious, Puzzle Racing at Center of the Universe Brewing Company is all about teamwork, laughter, and maybe a little friendly rivalry.
Pick a puzzle, start the clock, and see how fast you can go.
📅 Saturday, May 23, 2026
⏰ 1:00 – 7:00 PM
📍 Center of the Universe Brewing Co
11293 Air Park Rd, Ashland, VA 23005
🌳 MAY 28 — Woodland Cemetery Tour
If you’ve ever wondered about the stories tucked into Ashland’s past, this is a beautiful way to explore them.
Led by a knowledgeable guide, this walking tour through Woodland Cemetery offers a deeper look at the people and history that shaped this community. It’s quiet, meaningful, and surprisingly fascinating.
📅 Thursday, May 28, 2026
⏰ 5:30 PM
📍 Woodland Cemetery, Ashland, VA
🔗 ashlandmuseum.org
🎸 MAY 29 — HMB Rocks at Huddle Up
Some nights are just meant for live music and letting loose a little.
Head over to Huddle Up Sports Bar for a high-energy night with Hold My Beer — the kind of show where you sing along, laugh loud, and stay longer than you planned.
📅 Friday, May 29, 2026
⏰ 8:00 PM
📍 Huddle Up Sports Bar
🔗 https://www.huddleupsportsbar.com/
🍗 MAY 30 — Southern Food Festival
Come hungry — seriously.
The Southern Food Festival at Center of the Universe Brewing Company is packed with incredible food, live music, and that easygoing community energy we all love.
It’s the kind of day where you try something new, run into friends, and leave already planning to come back next year.
📅 Saturday, May 30, 2026
⏰ 12:00 – 7:00 PM
📍 Center of the Universe Brewing Co
11293 Air Park Rd, Ashland, VA 23005