Live Piano Music at The Sycamore
2025-08-05 18:00 - 21:00, 2025-08-07 18:00 - 21:00, 2025-08-08 18:00 - 21:00, 2025-08-09 18:00 - 21:00 (America/New_York) | 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.

Pub Trivia at Doherty's
2025-08-05 19:00 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for Pub Trivia every Tuesday, 7pm-9pm, hosted by Patrick W. Trivia. Trivia is free to play, with prizes for first, second, and third place.
See more events at Doherty’s.

Blues Jam at The MOD
2025-08-05 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 Tuesday, 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.

Pittsboro on the Patio
2025-08-06 08:30 - 10:00 | West End Kitchen and Catering, Pittsboro, North Carolina, 27312, United States
Join West End for Pittsboro on the Patio hosted every Wednesday, 8:30am-10am. During this community mixer event, enjoy complimentary fresh coffee from Pittsboro’s own Aromatic Roasters on the West End patio while meeting and creating great conversations with community members and leaders.
See more events at West End Kitchen and Catering.

Wake Up with The Chamber
2025-08-06 08:30 - 10:30 | Cowboy Cafe & Catering, North Dogwood Avenue, Siler City, North Carolina, 27344, United States
Make valuable connections for your business at Wake Up with The Chamber, hosted on the first Wednesday of each month, 8:30am-10:30am at Cowboy Cafe and Catering. Enjoy breakfast and networking with the Siler Area Chamber of Commerce. This event is $7 cash at the door or $8 online.

Live Music at Galloway's
2025-08-06 17:00 - 19:00, 2025-08-07 17:00 - 19:00, 2025-08-08 17:00 - 19:00, 2025-08-09 17:00 - 19:00 | 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.

IBN Evening Social at Thirsty Skull PBO
2025-08-06 18:00 - 19:30 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
After a long work day, unwind with friends and build your business referral network during monthly IBN Evening Socials at Thirsty Skull PBO. This event is hosted at Thirsty Skull Brewing – Pittsboro on the first Wednesday of every month, 6pm-7:30pm. Make sure to bring your business cards!
This meeting is free to attend. Food and drink are available for purchase (optional, not required, but you are encouraged to support the host establishment). Please bring a friend and a door prize (totally optional but fun). See more events at Thirsty Skull Brewing – Pittsboro. Part of the Chatham County Craft Beverages and Country Inns Trail.

Music Bingo at House of Hops
2025-08-06 18:00 - 20:00 | NC
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.

Monthly Markets at MOSAIC
2025-08-06 18:00 - 20:00 | MOSAIC at Chatham Park, 367 Freedom Parkway, Pittsboro, NC, 27312, United States
MOSAIC at Chatham Park hosts Monthly Markets every first Wednesday, Apr-Oct, 6pm-8pm. The MOSAIC Market aims to bring together a diverse array of handmade goods, artisanal creations, and farm-fresh offerings in one dynamic and engaging space. The event includes local growers and makers, craft beverage vendors, food trucks, and a special live music guest. This event is not just a market; it’s a gathering of like-minded individuals committed to quality, sustainability, and the beauty of artisanal craftsmanship.
Featured Chatham County vendors include bmc brewing, Hops & Berry Pittsboro, Havoc Brewing Company, Tacos Paraiso, and Red Moose Brewing Company. Say hello to 79° West while you’re there! At MOSAIC’s Markets, they will be hosting bands at the Works Yard Stage each night to provide additional marketing efforts and engagement from the community to create high traffic. The musical guest lineup is listed below:

Wed, Apr 2, 6pm-8pm Dorian Devins, Register.
Wed, May 7, 6pm-8pm The Jive Bombers, Register.
Wed, Jun 4, 6pm-8pm Geoff McBride, Register.
Wed, Jul 2, 6pm-8pm Daniel DeLorenzo, Register.
Wed, Aug 6, 6pm-8pm Popcorn Blue Band, Register.
Wed, Sep 3, 6pm-8pm Brown Mountain Lightning Bugs, Register.
Wed, Oct 1, 6pm-8pm Organ Failure, Register.

Monthly markets are held in The Works Yard Paeso. See more events hosted by MOSAIC at Chatham Park.

Jazz Nights at The Sycamore
2025-08-06 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.

Open Mic Night at Fair Game Beverage Company
2025-08-06 18:30 - 21:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Call all performing artists! Fair Game Beverage Company, located at The Plant in Pittsboro, hosts its Open Mic Night on the first Wednesday of every month, 6pm-9pm. Bring your talent – originals, covers, comedy, stories, or poetry! Or just come spectate and listen to local artists. Hosted by Danny Whipple.
Local NC beers, wines, ciders, and craft cocktails will be available at the bar. Local dining available at Kingston 99 Kitchen and Ta Contento. This event is free and takes place indoors. The Plant is wheelchair accessible, and additional accommodations are available upon request. Free parking is available on-site. No pets allowed, please. See more events at The Plant. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

Pittsboro Farmers Market
2025-08-07 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Pittsboro Farmers Market is open year-round and features select items from within a 50-mile radius. They are open every Thursday, 3pm-6pm, under the solar panels at The Plant. 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. Check out these upcoming markets:

Thu, Dec 18, 3pm-6pm Holiday Craft Market, featuring live music and local artisans and craftspeople along with your favorite regular market vendors.
Wed, Dec 31, 3pm-6pm New Year’s Eve Market. No market will be held on Thu, Jan 1, 2026 (New Year’s Day).

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 events at The Plant. See more farmers markets in our area.

Run Club at Thirsty Skull PBO
2025-08-07 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.

Music at Roost Beer Garden
2025-08-07 17:00 - 19:00, 2025-08-08 17:00 - 19:00 | Fearrington Village, 2000 Fearrington Village Center, Pittsboro, NC, 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 Thursdays and Fridays, 5pm-7pm. Please double-check their website to confirm – events are moved indoors or postponed during some weather conditions impacting 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

Opinionation Trivia at House of Hops
2025-08-07 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.

Briar Chapel Farmers Market
2025-08-08 16:00 - 18:00 | Briar Chapel
Briar Chapel Farmers Market is a recent endeavor, established at the beginning of 2023. Come to the Green of Great Meadow Park every Friday, 4pm-6pm, for healthy, wholesome food and farm products! 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.
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.

Weekly Free Tastings at Vino!! Wine Shop
2025-08-08 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro St, Suite D, 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.

Bynum Front Porch Music
2025-08-08 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. 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 one indoors if it rains). No pets or alcohol. Admission is free.
Upcoming Music Schedule
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.

Live Music: Orange County Allstars at City Tap
2025-08-08 19:30 - 21:30 | City Tap, 89 Hillsboro Street, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Orange County Allstars on Fri, Aug 8, 7:30pm-9:30pm.
This event takes place on the patio at The City Tap. There is no cover charge for this event, but tipping the musicians is recommended. See all events at City Tap.

Moonlight Movie Series at MOSAIC
2025-08-08 20:30 - 22:30 | Philip H. Kohl MOSAIC Family Commons, 457 Freedom Parkway, Pittsboro, NC, 27312, United States
Roll out the popcorn for the 2025 Moonlight Movie Series at MOSAIC, powered by Brightspeed! Join MOSAIC at Chatham Park for a night of cinematic magic under the stars. Relax with your favorite crew and enjoy classic flicks in an inviting outdoor setting. In the fall, experience their nostalgic Drive-In Movie Nights—where you can sip soda and munch popcorn from the confines of your car! Grab your lawn chairs and blankets and make some unforgettable memories.
The lawn opens an hour early, and the movie begins at the time indicated below. This event is FREE and open to the public, but registration is required. See the full schedule below and find your link to register:

Fri, Aug 8, 8:30pm-10:30pm Oppenheimer (Rated R), Register.
Fri, Sep 5, 8:30pm-10:30pm Avatar: The Way of Water, Register.
Fri, Sep 19, 7:30pm-9:30pm Transformers: Rise of the Beasts, Register.
Fri, Oct 3, 7:30pm-9:30pm Drive-In Movie: Wicked + Car Sing-a-long, Register.
Fri, Oct 17, 7pm-9pm Drive-In Movie: Moana, Register.
Fri, Oct 31, 7pm-9pm Drive-In Movie: Hocus Pocus 2 + Trunk-or-Treat, Register.

Anticipate bag checks and security screenings upon entry. Food or beverages purchased outside MOSAIC, weapons, and illegal substances are prohibited. Food and beverages will be available onsite for purchase – be prepared to present your receipt to event security. Bring a lawn chair or a blanket. Pets are welcome. This event is held outdoors on the Philip H. Kohl MOSAIC Family Commons. See more events hosted by MOSAIC at Chatham Park.

Chatham Mills Farmers Market
2025-08-09 10:00 - 13:00 | 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.

Summer in the Garden at FGS
2025-08-09 11:00 - 15:00 | For Garden’s Sake, 9197 Hwy 751 S, Durham, NC, 27713, United States
Join For Garden’s Sake for Summer in the Garden on Sat, Aug 9, 11am-3pm, hosted by Hummingbird Market! This magical outdoor market will be full of creativity, community, and summer charm. Admission is free.
What to expect:

30+ local makers and artists selling handmade goods and art.
Shop For Garden’s Sake’s summer annuals, perennials, houseplants, and more!
Raffles and scavenger hunts.
Kids’ gardening activity for purchase.
Food trucks serving up tasty bites.
Refreshing Sunset Slush and drinks are available for purchase at their Potting Shed Bar.

Bring a friend and enjoy a day of magic, makers, and community charm! The market will be outdoors. Bottled water will be available for purchase. The rain date is Sun, Aug 10, 11am-3pm. See more events at For Garden’s Sake.

Free Wine Tastings at The Belted Goat
2025-08-09 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 every Saturday, 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.
