Wake Up Wednesday at Carolina Brewery
2026-01-21 08:00 - 09:30 (America/New_York) | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Wake Up Wednesdays are hosted at Carolina Brewery & Grill every third Wednesday, 8am-9:30am. This networking includes breakfast, coffee, and new guest speakers each month. The fee to participate is $7 cash or $8 by card. If you do bring cash, do your best to bring exact change. If you pay by check, make it out to the Carolina Brewery. Please consider bringing a tip for your server.
This event takes place indoors. The bottom floor of the brewery is wheelchair-accessible, including entrances, parking, and restrooms. See more events at Carolina Brewery & Grill.

Live Music at Galloway's
2026-01-21 17:00 - 19:00, 2026-01-22 17:00 - 19:00, 2026-01-24 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.

Music Bingo at House of Hops
2026-01-21 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.

Jazz Nights at The Sycamore
2026-01-21 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
2026-01-21 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
2026-01-22 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.

Speed Networking Event at Hops and Berry
2026-01-22 17:00 - 19:00 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Join the Chatham County Chamber of Commerce for a Speed Networking Event at Hops and Berry on Thu, Jan 22, 5pm-7pm. Kick off the new year with an upbeat evening designed to help you make meaningful connections fast, while celebrating the launch of The Chatham Chamber’s new Chaymber Mobile App.
This event combines guided speed networking with a relaxed social atmosphere, making it easy to meet fellow local business owners, nonprofit leaders, and community partners. Whether you are new to our community or a longtime member, you will walk away with fresh connections, new visibility, and tools to stay engaged all year long.
WHAT TO EXPECT

Structured Speed Networking.
Short, facilitated rounds to help you meet a variety of people without the awkwardness of open mingling.
Mobile App Walk-Through & Launch Celebration.

Stick around after networking to continue conversations, enjoy great drinks, and build relationships in a relaxed setting. Come curious, bring your phone, and be ready to connect. Register for free!
This event takes place indoors at Hops and Berry. Free parking is available onsite. This space is wheelchair accessible. Schedules are subject to change – please confirm using the event organizer’s website for planning your visit. Part of MOSAIC at Chatham Park. See all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Opinionation Trivia at House of Hops
2026-01-22 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
2026-01-22 18:00 - 21:00, 2026-01-23 18:00 - 21:00, 2026-01-24 18:00 - 21:00, 2026-01-27 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.

Blues Jam at The MOD
2026-01-22 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.

Winter Art Sale at the Vineyard
2026-01-23 11:00 - 17:00, 2026-01-24 11:00 - 17:00, 2026-01-25 12:00 - 17:00 | FireClay Cellars, 1276 Bowers Store Rd, Siler City, NC, 27344, United States
Join FireClay Cellars for a Winter Art Sale at the Vineyard. Winter is a little more inspiring! Browse an eclectic exhibition of fine art from the collections of Kate Ladd, Lucy Harris, and Wilma Schroeder while sipping a glass of wine. They’ll be open throughout the winter for the following hours:

Fridays, 11am-5pm.
Saturdays, 11am-5pm.
Sundays, 12pm-5pm.

Free parking is available on site. The porch and first floor are ADA-compliant, with wheelchair-accessible parking. FireClay Cellars is part of the Chatham County Craft Beverages and Country Inns Trail. Discover more events at FireClay Cellars.

Weekly Free Tastings at Vino!! Wine Shop
2026-01-23 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.

Free Wine Tastings at The Belted Goat
2026-01-24 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.

Mead and Food Pairing Experience at Starrlight
2026-01-24 13:00 - 15:00 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
Join Starrlight Mead for a flavorful Mead and Food Pairing Experience on Sat, Jan 24, 1pm-3pm. In this guided tasting, you’ll sample a variety of Starrlight’s handcrafted meads, each paired with different flavors—salty, sweet, sour, and more—to discover how mead enhances food and how food transforms mead. Learn the art of pairing as you explore complementary and contrasting flavors, unlocking new ways to enjoy this ancient honey-based beverage. Whether you’re a seasoned mead lover or a curious foodie, this class will deepen your appreciation for the dynamic relationship between mead and cuisine. Cheers to a delicious adventure!
This experience is $25 per person for individuals ages 21 and over only. Starrlight Mead is part of The Plant. The space is wheelchair accessible, with parking and entry available behind the production facility. Additional free parking is available on-site. Pets are not allowed. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Vintage Nebbiolo: A Journey Through Time and Terroir
2026-01-24 14:00 - 15:00 | EB Wines, 40140 Moring, Chapel Hill, 27517, United States
Join EB Wines for Vintage Nebbiolo: A Journey Through Time and Terroir on Sat, Jan 24, 2pm-3pm. Explore the elegance and complexity of Italy’s noble Nebbiolo grape in this guided tasting experience. You’ll sample exceptional Nebbiolos from different regions and vintages, comparing them, and beyond. Discover how time, terroir, and tradition shape one of Italy’s most revered wines. Perfect for enthusiasts eager to deepen their appreciation of this iconic varietal.
The eighth annual series of Wine Tasting Classes comprises monthly sessions hosted by Esteban Brunello, owner of EB Wines. The classes are informative yet relaxed and open to guests with varying levels of knowledge, from novice wine drinkers to seasoned tasters. Classes are led by owner and wine director Esteban Brunello, who guides guests through the wine tasting process. Guests will learn to identify key wine notes, explore winemaking techniques, and receive recommendations for food pairings.
Tickets are $75 per person, and space is limited. This event takes place indoors. No pets are allowed. Free parking is available on-site. EB Wines is ADA-compliant. EB Wines is part of the Chatham County Craft Beverages & Country Inns Trail. See all events at EB Wines.

Live Music Sam Trebbing at House of Hops
2026-01-24 19:00 - 21:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops for Live Music with Sam Trebbing on Sat, Jan 24, 7pm-9pm.
This event takes place indoors. House of Hops is pet-friendly. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Live Music with Sam Frazier and The Side Effects at The MOD
2026-01-24 19:00 - 22:00 | The Modern Life Deli & Drinks, 46 Sanford Road, Pittsboro, NC, 27312, United States
Join The MOD for Live Music with Sam Frazier and The Side Effects on Sat, Jan 24, 7pm-10pm.
This event takes place indoors at The MOD. Free parking is available on the street and across the road from the Government Annex Building, as well as in the Justice Center Parking lot. This space is wheelchair accessible. 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.

Fearrington Farmers Market
2026-01-27 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
2026-01-27 18:00 - 20:00 | North Carolina
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.

Live Music: Mondo Guitaro at The City Tap
2026-01-27 18:00 - 20:00 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
Join The City Tap for Live Music with Mondo Guitaro on Tue, Jan 27, 6pm-8pm. “Lonesome Tones for High Plains Drifters”: Mondo Guitaro performs spaghetti western, surf, and 1960s-style instrumentals arranged for two guitars. Enjoy City Tap’s Tuesday night Supper Club Special, featuring a plated dish outside of their regular menu.
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, and there is a lift to the second floor and the service area located on the secondary staircase that connects to the patio. See all events at City Tap.

Music Bingo at Hops and Berry
2026-01-27 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
2026-01-27 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.

Coffee Klatch at Bynum Front Porch
2026-01-28 07:00 - 10:00 | Bynum General Store, 950 Bynum Rd, Bynum, NC, 27228, United States
Start your day with good coffee or tea and great conversation at Weekly Coffee Klatch with Bynum Front Porch Music, hosted every Wednesday, 7am-10am at the Historic Bynum General Store. Drop in for a warm cup, friendly faces, and casual community chats – everyone is welcome! Directions.
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.
