Pittsboro-Siler City Convention & Visitors Bureau

Weekly Free Tastings at Vino!! Wine Shop
2025-11-14 17:00 - 19:00, 2025-11-21 17:00 - 19:00 (America/New_York) | 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.

Run and Roam Fridays at The Plant
2025-11-14 17:00 - 21:00, 2025-11-21 17:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant after work and/or school for Run and Roam Fridays, hosted every Friday evening, Sep 5-Dec 12, 5pm-9pm. Come out for food and drink specials and plenty of family-friendly fun, including games, hula hoops, bubbles, chalk art, and more. 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.
This free event takes place indoors and 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, well-behaved pets are allowed outside; pet policies may vary by individual business. See all events at The Plant.

Live Piano Music at The Sycamore
2025-11-14 18:00 - 21:00, 2025-11-15 18:00 - 21:00, 2025-11-18 18:00 - 21:00, 2025-11-20 18:00 - 21:00, 2025-11-21 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.

8th Annual Oyster Roast at Carolina Brewery & Grill
2025-11-15 12:00 - 20:00 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Visit Carolina Brewery and Grill for their 8th Annual Oyster Roast on Sat, Nov 15, 12pm-8pm. Enjoy North Carolina Oysters from Ghost Fleet Oyster Co. along with live music on the patio and great cold beer. The live music schedule is as follows:

12:30pm-3pm The 8:59’s.
4:30pm-7pm The Petty Theives.

Part of the Chatham County Craft Beverages and Country Inns Trail. See all events at Carolina Brewery & Grill.

Tasting Classes with EB Wines
2025-11-15 14:00 - 15:00 | EB Wines, 40140 Moring, Chapel Hill, 27517, United States
The seventh annual Wine Tasting Classes is a collection of monthly wine tasting classes 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 various wine notes, discover techniques in the winemaking process, and receive recommendations for food pairings.
Mark your calendars for the following class dates:

Sat, Jul 26, 2pm-3pm Refreshing Whites.
Sat, Aug 23, 2pm-3pm Skin Contact.
Sat, Sep 20, 2pm-3pm Domestic Wines.
Sat, Oct 18, 2pm-3pm Obscure Reds.
Sat, Nov 15, 2pm-3pm Fall Reds.
Sat, Dec 13, 2pm-3pm Sparking – Petillant Naturel.

EB Wines is part of the Chatham County Craft Beverages & Country Inns Trail. See all events at EB Wines.

Live Music: Justin Abood at Havoc
2025-11-15 18:00 - 21:00 | NC
Havoc Brewing Company presents Live Music with Justin Abood on Sat, Nov 15, 6pm-9pm. Johnny Thai food truck will be on-site at Havoc 5pm-9pm.
This event is free and will take place both indoors and outdoors, weather permitting. There is no cover for entry, but tips for the musicians are encouraged. Free parking is available onsite. Pets are welcome. This space is wheelchair accessible. More events at Havoc Brewing Company. Part of the Chatham County Craft Beverages & Country Inns Trail.

Chestnut Roast and Cocktail Party
2025-11-15 18:00 - 21:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Get ready for The Plant’s third annual Chestnut Carnival with a Chestnut Roast and Cocktail Party on Sat, Nov 15, 6pm-9pm. Enjoy chestnut cocktails and chestnut rum cream from Fair Game Beverage Company, along with fresh roasted locally grown chestnuts! Bring your friends for a cozy fall evening featuring fireside chats, live music, and holiday vibes.
This event takes place indoors and 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, well-behaved pets are allowed. This event is free. See all events at The Plant.

Chestnut Carnival
2025-11-16 12:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Don’t miss The Plant’s third annual Chestnut Carnival on Sun, Nov 16, 12pm-6pm. For years, visitors to The Plant have entered the campus beneath a canopy of two giant chestnut trees. They were planted in 2005 and have become significant bearers of chestnut fruit. There will be roasted chestnuts, chestnut shelling demonstrations, chestnut trees for sale at Rachel’s Native Plants, chestnut cocktails from Fair Game Beverage Company, and chestnut beer from Fullsteam Brewing. On-demand Chestnut Carnival shirts will be available from Hempsmith Clothing Company. Chestnut dishes will be on the menu at Kingston 99 Kitchen.
This event takes place indoors and 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 but discouraged. This event is free. See all events at The Plant.

Live Music: Lee Gildersleeve & The Bad Dogs Blues Band
2025-11-16 14:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Lee Gildersleeve & The Bad Dogs Blues Band. Performances take place on the following dates:

Sun, Jun 15, 1pm-4pm.
Sat, Sep 13, 5pm-8pm.
Sun, Nov 16, 2pm-5pm.

Lee Gildersleeve was in the first wave of young blues rock guitarists that emerged in the 1960s’ blues revival. In over four decades of performing, Lee’s guitar playing has been featured with rock and roll legends Chuck Berry and Bo Diddley, rocker George Thorogood, rockabilly icon Sleepy La Beef, blues divas Koko Taylor and Marcia Ball, L.A. legend Stacy Robin, and scores of talents from coast to coast. His current band, the Bad Dogs, covers a wide range of material from Lowell Fulsom, Bo Diddley, Little Richard, Muddy Waters, and Rufus Thomas, along with many of his own original numbers. Jordan Lawrence of The Independent recently wrote, “If you’re looking for a lesson in how the blues first bled into rock ‘n’ roll, you’ll find a living demonstration in singer-guitarist Lee Gildersleeve.” As Bo Diddley said of Lee, “He gets it.” And you will too.
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they are in a position of having to cancel, they will try to do so well in advance. 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.

Euchre Mondays at bmc
2025-11-17 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.

Fearrington Farmers Market
2025-11-18 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
2025-11-18 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
2025-11-18 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
2025-11-18 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.

Wake Up Wednesday at Carolina Brewery
2025-11-19 08:00 - 09:30 | 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.

Sip and Shop Event at Vino!!
2025-11-19 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for a Sip and Shop Event on Wed, Nov 19, 5pm-7pm. To help kickstart your holiday shopping, Vino!! is bringing in two local vendors, Kendra Brower of Blue Blaze Jewelry and Terri Rebey of Gigi’s Candy Jar, who will be selling some of their products. Earrings, bracelets, truffles, turtles, oh my!
Not only will Kendra and Terri be in their shop, but they will also carry a plethora of other gift-giving goodies – wine (of course), cheeses, tinned fish, olives, hot sauce, nuts, pasta, wine tools, gift certificates, and more! Wednesday is “no corking fee” day, so bring a friend and enjoy your favorite bottle while you browse the shop for gifts for others or yourself!
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Music Bingo at House of Hops
2025-11-19 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.

Jazz Nights at The Sycamore
2025-11-19 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
2025-11-19 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
2025-11-20 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.

Wine Class – Walls of Walla Walla
2025-11-20 18:00 - 19:00 | Fearrington House Restaurant, 230 Market Street, Pittsboro, 27312, United States
Join Fearrington Village for a Wine Class – Walls of Walla Walla on Thu, Nov 20, 6pm-7pm. Nestled between the Blue Mountains and ancient basalt walls, the Walla Walla Valley has grown from wheat fields and orchards into one of America’s most exciting wine regions. Wine Director Troy Revell will help uncover how geology, climate, and pioneering winemakers have shaped Walla Walla’s bold reds and elegant whites. Explore the unique sub-regions, discover why Syrah and Cabernet Sauvignon thrive there, and taste wines that reveal the character of this remarkable valley straddling Washington and Oregon.
A few small bites from Chef Gagne are included, and wines tasted will be available for purchase at the end of the event. The class will take place on the Terrace behind The Fearrington House Restaurant. This $75 all-inclusive wine class is non-refundable. If your plans have changed, please feel free to send a lucky friend in your place! Just send Fearrington an email with their name or have them bring your confirmation email.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Opinionation Trivia at House of Hops
2025-11-20 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.

Blues Jam at The MOD
2025-11-20 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.

3rd Friday Artist Receptions
2025-11-21 17:00 - 20:00 | Pittsboro Gallery of Arts, 44 Hillsboro Street, Pittsboro, NC, 27312, United States
Pittsboro Gallery of Arts is pleased to announce the return of 3rd Friday Artist Receptions. Each month, they highlight a new artist and offer an opportunity to meet them and ask about their work. Beverages and snacks will accompany. These events are held every third Friday, 5pm-8pm. Featured artists are announced on their Facebook Page.
See more Pittsboro Gallery of Arts events.
