Pittsboro-Siler City Convention & Visitors Bureau

Live Music at Galloway's
2026-05-20 17:00 - 19:00, 2026-05-21 17:00 - 19:00, 2026-05-23 17:00 - 19:00 (America/New_York) | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village, for live music, local beer on tap, and wine by the glass Wednesday-Saturday, 5pm-7pm. Check out their events calendar to see who’s playing.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Music Bingo at House of Hops
2026-05-20 18:00 - 20:00 | North Carolina
Join House of Hops every Wednesday, 6pm-8pm for Music Bingo hosted by DJ Special K. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Crokinole at Fair Game
2026-05-20 18:00 - 20:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Try your hand at an obscure Canadian board game with Crokinole at Fair Game Beverage Company, hosted every third Wednesday, 6pm-8pm in the Wheelhouse. Crokinole is a classic Canadian tabletop game — think shuffleboard meets curling, shrunk onto a round wooden board. It’s easy to learn in a single round and genuinely fun whether you’re a first-timer or a seasoned shooter, and newcomers are always welcome.
Here’s how it works: Two players (or four, in teams) sit across from each other and take turns flicking small wooden discs from the outer edge toward the center of the board. The bullseye is a recessed hole in the middle worth 20 points; concentric scoring rings count for less the farther out you land. Guarding the center is a ring of eight small pegs that your disc has to navigate around.
If your opponent has any discs on the board, your shot has to hit one of them. Miss, and your disc is removed. If the board is clear, you have to land inside the innermost peg ring, or your disc comes off. So every turn is a choice between attacking your opponent’s pieces and quietly racking up points of your own. Discs are scored once all of them have been played, and the higher total wins the round.
Come early to sip and shop the Chatham Beverage District, part of the Chatham County Craft Beverages & Country Inns Trail, with local beers from bmc brewing, wines and ciders from Starrlight, spirits from Fair Game, and sake from Koshu. Local dining available at Kingston 99 Kitchen and Ta Contento.
Free parking is available on-site. This free event takes place indoors in the Fair Game Wheelhouse. Leashed, well-behaved pets are allowed outside; pet policies indoors vary by individual business. The Plant is accessible to guests and will do its best to accommodate any additional requests. Please contact music@theplantnc.com with any accommodation requests or accessibility concerns. See all events at The Plant. See all events at Fair Game Beverage Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Jazz Nights at The Sycamore
2026-05-20 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Wednesday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Jazz Nights every Wednesday, 6pm-9pm. The series features a rotating list of local musicians. The Sycamore also offers their Lounge Menu in the dining room on Wednesday nights. Reservations are highly recommended. Past and present musicians include the Steve Hobbs Trio, Lauren Meehan, Dave Quick Jazz, and the Tony Galiani Jazz Quartet. See the upcoming lineup here.

Karaoke at Hops and Berry
2026-05-20 19:00 - 22:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Karaoke every Wednesday, 7pm-10pm. The taproom’s weekly Karaoke night turns its live-entertainment stage over to the crowd, where regulars and first-timers alike line up to belt out their favorites—whether that’s a power ballad, a crowd-singalong anthem, or a deep cut only you remember. With a supportive, come-as-you-are vibe, it’s as fun to cheer from a table as it is to step up and perform.
This event is free and takes place indoors. Free parking is available onsite. This space is wheelchair accessible. Part of MOSAIC at Chatham Park. See more events at Hops & Berry. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

12th Annual Chatham County Golf Classic
2026-05-21 09:00 - 14:00 | Chapel Ridge Golf Club, 1010 Chapel Ridge Dr, Pittsboro, NC, 27312, United States
Golfers, grab your clubs for a day of fun and fellowship for a good cause as the Central Carolina Community College Foundation hosts its 12th Annual Chatham County Golf Classic on Wed, May 21, 9am-2pm at Chapel Ridge Golf Club. The format for the Chatham County Golf Classic is four-person Captain’s Choice. Prizes will be awarded to the top teams in each flight. Shotgun starts at 9am, with lunch from 1pm-2pm.
The Chatham County Golf Classic registration form can be downloaded from the Foundation’s website. Registration is also available by contacting CCCC Director of Community Engagement Alexandra Dowdy at (919) 718-7338 or by email at adowdy@cccc.edu.
The proceeds from the Golf Classic will be used to help provide scholarships and other financial assistance. The CCCC Foundation is a 501(c)(3) charitable organization affiliated with, but independent of, Central Carolina Community College. It receives donations of money and equipment on behalf of the college and uses them to promote its educational mission and assist students through scholarships and grants.
See more Chatham Sports Alliance events.

Pittsboro Farmers Market
2026-05-21 15:00 - 18:00 | Pittsboro Pop-Up Park, West Salisbury Street, Pittsboro, North Carolina, 27312, United States
The Pittsboro Farmers Market is open year-round and features select items from within a 50-mile radius. They are open every Thursday, 3pm-6pm at Pittsboro’s Pop-Up Park. The product-only market features baked goods, eggs, flowers, honey, jams/jellies, soaps, plants, poultry, and other meats. Vendors include Celebrity Dairy, In Good Heart Farm, and Vortex Roasters. Many chefs at restaurants in our area network with Pittsboro Farmers Market vendors, including Kingston 99 Kitchen and West End Kitchen & Catering. You can find a complete, up-to-date list of vendors here.
Special markets are hosted on occasion.
The Pittsboro Farmers Market takes place outdoors, rain or shine. Leashed, well-behaved pets are allowed. Entry is free. Bringing your own bags, cash, and a cooler for perishable items is advised. The market is held on a gravel lot beneath the solar panels, with free parking available nearby. See more farmers markets in our area.

Run Club at Thirsty Skull PBO
2026-05-21 17:00 - 18:30 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro every Thursday, 5pm-6:30pm for Run Club.
See all events at Thirsty Skull Brewing – PBO. Part of the Chatham County Craft Beverages & Country Inns Trail.

NoVi Vibes and Bites
2026-05-21 17:30 - 19:30 | The NoVi Green, 175 Parkland Drive, Pittsboro, 27312, United States
Get ready for Novi Vibes and Bites, hosted Thu, May 21 and Thu, Jun 18, 5:30pm-7:30pm. This event features live acoustic music by a local solo singer-guitarist, along with a rotating lineup of food trucks. Enjoy dinner on the Green, listen to live music, and spend the evening connecting with neighbors.
This outdoor event is open to the community and free to attend. Food and beverages are available for purchase. In the event of inclement weather, live music will be canceled; the food truck will remain as scheduled. Check Chatham Park’s social media channels for updates. See more NoVi events.

Opinionation Trivia at House of Hops
2026-05-21 18:00 - 20:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops every Thursday, 6pm-8pm for Opinionation Trivia. This Family Fued-style trivia game is so much fun! Play at 6pm and again at 7pm for two chances to win $15 or $25 House of Hops gift cards. Bring the crew, bring food from neighbors Cafe Root Cellar or Mi Cancun, and enjoy!
More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Piano Music at The Sycamore
2026-05-21 18:00 - 21:00, 2026-05-22 18:00 - 21:00, 2026-05-23 18:00 - 21:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Every Tuesday, Thursday, Friday, and Saturday night, 6pm-9pm, The Sycamore at Chatham Mills hosts live Live Piano Music. The series features a rotating list of local musicians. Past and present musicians include Kris Whitenack, Robert Griffin, Lindsey Rosebrook, and Stephanie Schmitt. See the upcoming lineup here.
See more events at The Sycamore at Chatham Mills.

Live Music with Mondo Guitaro at Thirsty Skull
2026-05-21 19:00 - 21:00 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
Join Thirsty Skull Brewing – Pittsboro for Live Music with Mondo Guitaro, hosted every third Thursday,7pm-9pm. Come hang out and listen to the awesome sound of Mondo Guitaro. “Lonesome Tones for High Plains Drifters”: Mondo Guitaro performs spaghetti western, surf, and 1960s-style instrumentals arranged for two guitars. You won’t want to miss this!
There is no cover charge. Craft beer and glasses of wine from Thirsty Skull’s selection will be available for purchase. Ages 21 and older only.
See more events at Thirsty Skull Brewing – Pittsboro. Part of the Chatham County Craft Beverages and Country Inns Trail.

Blues Jam at The MOD
2026-05-21 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Blues Jam hosted every Thursday, 7pm-10pm by Lo Taylor. This open jam is an excellent opportunity for those who share a love for the blues and wish to share their talents. Mr. Taylor and his band of talented musicians will make you feel right at home on our stage. Bring your voice, bring your instruments, or just bring your ears to partake in this musical delight. The Mod is dedicated to providing space for live music, great food, craft beverages, community, and love. Arrive early for musician sign-up or to grab a table for the evening. Any schedule changes due to weather, holidays, or unforeseen circumstances will be posted on their Facebook and Instagram pages.
See more events at The MOD.

Free Public Domain Movie Night at bmc
2026-05-21 19:00 - 22:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join bmc brewing for a Free Public Domain Movie Night hosted every Thursday, 7pm-10pm. Films enter the public domain in the United States when their copyright protection expires, which typically happens 95 years after publication for older works, or if owners fail to follow registration and renewal requirements. As of 2026, all films released before 1930 are in the public domain. Stay tuned for some classics!
This indoor event is free. The space is wheelchair accessible. No pets are allowed. Free parking is available on-site. bmc brewing is part of The Plant. See all events at The Plant. See all events at bmc brewing. Part of the Chatham County Craft Beverages & Country Inns Trail.

Briar Chapel Farmers Market
2026-05-22 16:00 - 18:00 | Great Meadow Park, 161 Salt Cedar Lane, Chapel Hill, NC, 27516, United States
Briar Chapel Farmers Market is a recent endeavor, established at the beginning of 2023. Come to the Green of Great Meadow Park every Friday, Mar-Dec, 4pm-6pm!
Shoppers will find fresh seasonal produce, pasture-raised meats, native plants, local honey, baked goods, and prepared foods, much of which is harvested or made in the surrounding region. Familiar faces include growers offering peak-season vegetables, a farm bringing pastured lamb and pork, and bakers known for gluten-free cakes and breads. See the complete list of vendors here. On the last Friday of every month, they host an Artisan Market featuring a diverse range of vendors from within and outside the community.
For visitors, it’s an easy and welcoming way to experience Chatham County’s strong local food culture and meet the community behind it. Whether you’re stocking up on the freshest produce around or simply soaking in the relaxed, neighborly atmosphere, the Briar Chapel Farmers Market reflects the unhurried, locally rooted character that defines this corner of the county.
Briar Chapel Community Association (BCCA) is a homeowner-controlled, planned community in Chapel Hill, North Carolina. As an award-winning community, Briar Chapel offers resort-style amenities, thoughtfully designed homes, social events, beautiful trails, and more. See more Briar Chapel events.

Fridays at The Farm
2026-05-22 16:00 - 21:00 | Old Mill Farm, 8913 NC-751, Durham, 27713, United States
Join Old Mill Farm for Fridays at The Farm, hosted every Friday night, March-November, 4pm-9pm. Enjoy family-friendly live music and activities on their quaint Century Farm. Grab a Season Pass while they are still available to gain access to all 2026 shows! Gates open at 4pm, and live music starts at 9pm. The event features a rotating selection of musicians and food trucks – check their website for performers and food trucks.
Please note that if tickets are not available for a given date, they are SOLD OUT. Drive-ins will not be accommodated on those days. Please plan accordingly. Single-day admission is $22.50 per car if pre-booked online or $30 at the gate. Admission includes parking for one vehicle, admission for all guests in your vehicle, access to petting areas, lawn games, and play areas, and live music. Food trucks and beverages are available for purchase. Free parking is available onsite. No outside alcohol is allowed. No pets allowed, except for ESA and Service Animals. See more events at Old Mill Farm.

Weekly Free Tastings at Vino!! Wine Shop
2026-05-22 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Weekly free tastings at Vino!! Wine Shop are hosted every Friday. Experts share their picks of wines with varied pricing and from diverse locations. Tasting details, including which wines will be served, are shared on their Facebook Page and in their newsletters.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Music at Roost Beer Garden
2026-05-22 17:00 - 19:00 | Roost Beer Garden, 270 Market Street, Pittsboro, 27312, United States
Visit Roost Beer Garden at Fearrington Village, a seasonal beer garden, for live music on the porch, local beer on tap, wine by the glass, and artisan wood-fired pizza (4pm-7pm). Pull up a chair around the water fountain or under large oaks, and enjoy good weather and good company.
Music is typically hosted April-October on Fridays, 5pm-7pm. Please double-check their website for featured musicians and to confirm whether events are moved indoors or postponed during weather conditions that affect outdoor music and activities.
MENU – WOOD-FIRED PIZZAS
Red

Mozzarella…Fresh Mozzarella, Micro Basil
Pepperoni…Mozzarella, Sauce
Prosciutto…Prosciutto, Green Olives
Carne…Housemade Sausage, Soppressata, Pepper Jam, Asiago, Croutons

White

Mushroom Carbonara…Wild Mushrooms, Pancetta, Caramelized Onions, Confit Garlic, Egg Yolk, Truffle Oil
Six Cheese Pizza…Mozzarella, Fontina, Rosemary Ricotta, Parmesan, Provolone, Pecorino

Bynum Front Porch Music
2026-05-22 19:00 - 20:30 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
The Bynum Front Porch Music Series takes place every Friday, May-Aug, 7pm-8:30pm at the Historic Bynum General Store, featuring a variety of bands spanning multiple musical genres, including gospel, folk, blues, rockabilly, and bluegrass. You can park at the Bynum ball field or in the field adjacent to the store. Doors open at 6:30pm, and food trucks are on-site. Directions. There is an outdoor stage (and an indoor one if it rains). No pets or alcohol. This event is open to the public and admission is free – no tickets required. A hat is passed around to collect contributions. There is usually at least one food vendor on-site.
2026 SCHEDULE

Fri, May 1, 7pm-8:30pm Secret Monkey Weekend.
Fri, May 8, 7pm-8:30pm John Howie, Jr.
Fri, May 15, 7pm-8:30pm Orange County Lockdown.
Fri, May 22, 7pm-8:30pm Gravy Boys.
Fri, May 29, 7pm-8:30pm The Old Ceremony.
Fri, Jun 5, 7pm-8:30pm Jack The Radio.
Fri, Jun 12, 7pm-8:30pm Dub Lorenzo.
Fri, Jun 19, 7pm-8:30pm Them.
Fri, Jun 26, 7pm-8:30pm Kit McCay.
Fri, Jul 3: NO MUSIC – ENJOY THE 4TH!
Fri, Jul 10, 7pm-8:30pm Mad Crush.
Fri, Jul 17, 7pm-8:30pm GrassStreet.
Fri, Jul 24, 7pm-8:30pm Bulltown Strutters.
Fri, Jul 31, 7pm-8:30pm Graymatter.
Fri, Aug 7, 7pm-8:30pm A Different Thread.
Fri, Aug 14, 7pm-8:30pm Nine Times Around.
Fri, Aug 21, 7pm-8:30pm Deep Chatham Ramblers.
Fri, Aug 28, 7pm-8:30pm Bluegrass Experience.

Year-round events, including a Christmas tree sale and a holiday bazaar. See a feature about geocaching in Bynum, produced by UNC-TV for NC Weekend and sponsored in part by the NC Division of Tourism, Film, and Sports Development. See more events at Bynum General Store.

Live Music: Sonic Blues at The City Tap
2026-05-22 19:30 - 21:30 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Sonic Blues, hosted on the following dates:

Fri, May 22, 7:30pm-9:30pm.
Sat, Jul 25, 7:30pm-9:30pm.

On Saturdays, enjoy $3.50 mimosas or a bottle for $12.50, with your choice of orange, pineapple, cranberry, or grapefruit juice.
This event takes place at The City Tap. There is no cover charge for this event, but tipping the musicians is recommended. The patio is wheelchair-accessible from the back of the building. There is a lift to the second floor, and the service area is located on the secondary staircase that connects to the patio. See all events at City Tap.

Chatham Mills Farmers Market
2026-05-23 08:00 - 12:00 | Chatham Mills, 480 Hillsboro Street, Pittsboro, NC, 27312, United States
Chatham Mills Farmers Market takes place every Sat, Apr-Oct, 8am-12pm and Nov-Jan, 10am-1pm. It’s a growers-only market featuring fresh veggies, fruits, meats, eggs, baked goods, preserved foods, perennial plants and garden starters, handmade crafts, and more. Takes place in the front parking lot and the lawn in front of Chatham Mills.
Vendors include Chatham Oaks Farm. Sponsors include Chatham Marketplace, Country Farm & Home, French Connections, and New Horizons Downtown.
Interested vendors should fill out the applicable form and mail it, along with the application fee, to Chatham Mills Farmers’ Market, PO Box 1571, Pittsboro, NC 27312. If you would like to attend the market as a visiting vendor during one of their special events, contact the Market Manager at cmfmmanager@gmail.com about signing up – no formal application is required. See more events at Chatham Mills.

Cups and Pups
2026-05-23 08:00 - 13:00 | The NoVi Green, 175 Parkland Drive, Pittsboro, 27312, United States
Join NoVi for Cups and Pups, hosted every Saturday in May, 8am-1pm. Start your morning with a fresh cup from The Saddle Roast coffee truck and bring your four-legged friend along for the fun. Whether you’re heading out after a workout at the Chatham Park YMCA or just looking for a cozy coffee stop, this is the perfect excuse to slow down and say hi to neighbors (and pups). Grab a coffee, enjoy a pup treat on NoVi, and take a stroll around NoVi while you are here. The full schedule is listed below:

Sat, May 2, 8am-1pm.
Sat, May 9, 8am-1pm.
Sat, May 16, 8am-1pm.
Sat, May 23, 8am-1pm.
Sat, May 30, 8am-1pm.

This free, pet-friendly event takes place outdoors. See more NoVi events.

Women's Week Camp at Clapping Hands Farm
2026-05-23 09:00 - 16:00 | Clapping Hands Farm, 3348 Alston Chapel Road, Pittsboro, NC, 27312, United States
The Women’s Week Camp at Clapping Hands Farm, hosted Sat, May 23-Wed, May 27, 9am-4pm, is about creativity, relaxation, and sisterhood in equal measure. You’ll feel rested, nurtured, befriended, and inspired. Camp days will include movement, thanksgiving, play, a selection of different workshops, leisurely lunches, a check-in with a small group, and circles to begin and end the day. Along with lots of permission to do what you are called to do, including a lot of beautiful “nothing” if that is what you choose, Clapping Hands Farm invites you to bring home a new commitment to yourself and the things that make you happy.
Louise Omoto Kessel will be your guide for this week, along with an excellent selection of guest artists. Louise is a storyteller and a printmaker, and she loves to felt, collage, and make all manner of things. She is also the founder and director of Clapping Hands Farm and the mother of two young adults.
Trans, non-binary, gender-fluid, and gender-creative humans who want to participate in Women’s Week Camp are welcome! Ages 18+ are welcome. The cost is $325 per person. Scholarships are available, and no one is turned away. Chatham County residents receive a $25 discount. You may sign up by the day. It’s ideal for everyone to come on Saturday and to come for at least 2 days, but they will work with your schedule. The cost is $65 per day. Register here. See more events at Clapping Hands Farm.

Memorial Day Brunch at Carolina Brewery & Grill
2026-05-23 10:00 - 14:30 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Join Carolina Brewery & Grill for a Memorial Day Brunch on the following dates:

Sat, May 23, 10am-2:30pm.
Sun, May 24, 10am-2:30pm.
Mon, May 25, 10am-2:30pm.

This annual celebration coincides with the launch of Carolina Brewery’s new seasonal menu, with items including:

Jalapeño Poppers with house-made pimento cheese, bacon, and cotija.
A Slider Sampler Platter featuring cheeseburger, fried chicken, and pork belly sliders.
Rainbow Salad with romesco-glazed chicken and blueberries.
Steak Protein Bowl with blackened steak kabobs and Carolina Brewery’s new Western Carolina BBQ sauce.
The Romesco Burger with goat cheese and balsamic caramelized onions.

The menu pairs perfectly with Carolina Brewery beers, including the return of the seasonal Sky Peach Kölsch, a light, refreshing summer beer perfect for cookouts, patio hangs, and holiday weekend gatherings. Carolina Brewery’s new Western Carolina BBQ sauce also debuts on the seasonal menu, bringing smoky-sweet regional North Carolina barbecue flavor to several dishes.
Free parking is available onsite. The downstairs space and patio are both wheelchair-accessible, including wheelchair-accessible parking, seating, entrances, and restrooms. Leashed, well-behaved pets are allowed only on the patio. Part of the Chatham County Craft Beverages & Country Inns Trail. See more events along the trail. See more events at Carolina Brewery.

Saturday Slowdown at Old Mill Farm
2026-05-23 11:00 - 15:00 | Old Mill Farm, 8913 NC-751, Durham, 27713, United States
Join Old Mill Farm for a Saturday Slowdown on Sat, May 23, 11am-3pm. Start your weekend off right with some time on the farm! Visit your favorite farm animals, catch some fish in the pond, have a picnic, and more. Enjoy free admission! This is a great time to enjoy the farm on a slower day. There will NOT be live music or a food truck on this day.
Free parking is available onsite. No outside alcohol is allowed. No pets allowed, except for ESA and Service Animals. See more events at Old Mill Farm.

Free Wine Tastings at The Belted Goat
2026-05-23 13:00 - 15:00 | The Belted Goat, Market Street, Pittsboro, North Carolina, 27312, United States
Visit The Belted Goat/Galloway’s Bar at Fearrington Village for free wine tastings select Saturdays, 1pm-3pm. Tastings will vary depending on when you visit, so please check their calendar before planning your visit.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.
