Wake Up with The Chamber
2025-07-02 08:30 - 10:30 (America/New_York) | 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.

IBN Evening Social at Thirsty Skull PBO
2025-07-02 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
2025-07-02 18:00 - 20:00, 2025-07-09 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
2025-07-02 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
2025-07-02 18:00 - 21:00, 2025-07-09 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
2025-07-02 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. See all events at Fair Game Beverage Company. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

Karaoke at Hops and Berry
2025-07-02 19:00 - 22:00, 2025-07-09 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.

Run Club at Thirsty Skull PBO
2025-07-03 17:00 - 18:30, 2025-07-10 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.

Opinionation Trivia at House of Hops
2025-07-03 18:00 - 20:00, 2025-07-10 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
2025-07-03 18:00 - 21:00, 2025-07-04 18:00 - 21:00, 2025-07-05 18:00 - 21:00, 2025-07-08 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.

4th of July at The Plant
2025-07-04 14:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Come out for 4th of July at The Plant on Fri, Jul 4, 2pm-8pm. They have a fun celebration planned for the family featuring live music, yard games, sprinklers, and of course, delicious food and beverages.
This event takes place outdoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed pets are allowed. This event is free. See all events at The Plant.

Weekly Free Tastings at Vino!! Wine Shop
2025-07-04 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.

The Wanderer's Market
2025-07-06 12:00 - 16:00 | West End Kitchen and Catering, Pittsboro, North Carolina, 27312, United States
Join West End for The Wanderer’s Market hosted every first Sunday, May-Oct, 12pm-4pm. Markets include a new music guest each month, great food and drink from West End, and shopping at Finders and Seekers Emporium.
See more events at West End Kitchen and Catering.

Pittsboro Summer Fest
2025-07-06 16:00 - 21:00 | Pittsboro Pop-Up Park, West Salisbury Street, Pittsboro, North Carolina, 27312, United States
The Pittsboro Business Association presents Pittsboro Summer Fest on Sun, Jul 6, 4pm-9pm. Activities include a Decorated Bicycle Parade, juggling, giant balloons, hula hooping, balloon animals, a duck pond for prizes, axe throwing, and more. There will also be food trucks and local vendors. Enjoy live music from local and regional musicians. Popular events include a Watermelon Seed Spitting Contest, a Pie Contest, and a Beard and Mustache Contest. To enter, email your name and contact information to downtown.pittsboro@gmail.com. Winners will be announced at 6:45pm.
The Chatham County Historical Association wouldn’t miss Pittsboro’s Summerfest, and you shouldn’t either! Stop by their table to say hi, and be sure to bring your own stories about Old Chatham County—they’d love to hear them!

Euchre Mondays at bmc
2025-07-07 18:00 - 20:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
Join a fantastic group of Euchre enthusiasts every Monday, 6pm-8pm, for Euchre Mondays. This weekly gathering is built around the classic trick-taking card game. No experience is needed — a fantastic regular euchre group is happy to bring newcomers up to speed, so you can show up solo or with friends and jump right in. Monday doubles as $5 pint night at bmc brewing, so you can pair your hand of cards with one of the 18 beers bmc brews on site, alongside hard cider, hard seltzer, wine, and non-alcoholic options.
The event is free and takes place indoors. The space is wheelchair accessible, and on-site parking is free. Pets are not permitted indoors at bmc brewing. bmc brewing is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

$10 Tuesday Tastings at Fair Game
2025-07-08 10:00 - 20:00 | Fair Game Beverage Company, 192 Lorax Lane, Pittsboro, NC, 27312, United States
Fair Game Beverage Company hosts $10 Tuesday Tastings every Tuesday, 10am-8pm. Come out on Tuesdays and enjoy a tasting of your choice of their housemade spirits, Whiskey, liquors, or NC beer/wine/cider flights.
This event takes place indoors. The Plant is accessible to guests and will do its best to accommodate any additional requests—contact music@theplantnc.com with any accommodation requests or accessibility concerns. There is free parking. Leashed pets are allowed but discouraged. See all events at The Plant.

Fearrington Farmers Market
2025-07-08 15:00 - 17:00 | Fearrington Farmers Market, E Camden, Pittsboro, NC, 27312, United States
The Fearrington Farmers Market is a producers-only market open Mar-Oct, Tuesdays, 4pm-6pm, and Nov-Feb, Tuesdays, 3pm-5pm, year-round in Fearrington Village. Bring reusable tote bags and plan to explore the many local vendors. You also might chat with the farmers, see old friends, or meet new ones! It’s a welcoming, inclusive, and friendly atmosphere that encourages healthy, happy living.
Fearrington Farmers Market has more than 3 dozen members and is now in its 30th season. Not all vendors are there every week, but some vendors are there every week, year-round. Each market features live music. Vendors include Celebrity Dairy, In Good Heart Farm, and bmc brewing. See their full list of vendors.
Come early if you’d like to review what is being offered; sales begin at the scheduled time, signaled by the bell. Bring along small bills ($20 or lower) to pay for your purchase. Some vendors accept credit and debit cards, and most will accept checks. This event takes place outdoors, rain or shine. Entry is free. Leashed, well-behaved pets are welcome. See more events at Fearrington Village.

Run Club at House of Hops
2025-07-08 18:00 - 20:00 | NC
Join House of Hops every Tuesday, 6pm-8pm for Run Club and 20%-off mixed six pack. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at Hops and Berry
2025-07-08 19:00 - 21:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come to Hops and Berry-Pittsboro for Music Bingo every Tuesday, 7pm-9pm. Instead of numbers, players listen for tracks and mark their cards as they recognize each tune, racing to fill a line before anyone else. It’s a low-key, high-energy way to spend a weeknight, and the format welcomes everyone from casual listeners to die-hard music buffs.
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.

Pub Trivia at Doherty's
2025-07-08 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
2025-07-08 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.

Poetry at The Plant
2025-07-09 18:00 - 19:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Come out for Poetry at The Plant on the second Wednesday of every month, 6pm-7pm. Enjoy an hour of original poetry from regional poets in the Fair Game Beverage Company Wheelhouse Tasting Room (and enjoy a drink and meal while you’re at it)!
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. See more events at Fair Game Beverage Company. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.
