Pittsboro-Siler City Convention & Visitors Bureau

Live Piano Music at The Sycamore
2025-08-30 18:00 - 21:00, 2025-09-02 18:00 - 21:00, 2025-09-04 18:00 - 21:00, 2025-09-05 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.

Starrlight's Big 15th Birthday Party!
2025-08-31 12:00 - 17:00, 2025-09-01 12:00 - 18:00 | Starrlight Mead, 130 Lorax Ln, Pittsboro, NC, 27312, United States
This year, come on out for Starrlight’s Big 15th Birthday Party on the following dates:

Sat, Aug 30, 12pm-6pm.
Sun, Aug 31, 12pm-5pm.
Mon, Sep 1, 12pm-6pm.

What’s a birthday without cake? Starrlight will include cake with each paid tasting for the entire weekend. Tastings are $14 per person. Pairings are below:

Off-dry blueberry mead with a dark chocolate brownie.
Coffee mead with a mini-chocolate chip shortbread cookie.
Semi-sweet traditional mead with cheesecake from Phoenix Bakery.
Spiced apple mead with a cream cheese frosting-topped spice cake.

You can also taste their new Chocolate Orange Reserve for $1.50 (regularly $3) or the Ebling Reserve for FREE (regularly $3). Plus, it may be Starrlight’s birthday, but you get the presents! Check out these incredible discounts:

10% off a half-case of mead (6 bottles).
15% off a full case of mead (12 bottles).
20% for Mead Club Members!

Plus, there will be fun giveaway drawings and presents!
Starrlight Mead is part of The Plant. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Pawpaw Palooza at The Plant
2025-08-31 12:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for their first Pawpaw Palooza on Sun, Aug 31, 12pm-6pm. Come out and celebrate this unique and delicious fruit! There will be Pawpaws for sale, Pawpaw cocktails, pop-up vendors, and more. Interested in being a vendor? Sign up here.
This event takes place outdoors. 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. There is free parking. Leashed pets are allowed. This event is free. See all events at The Plant.

Labor Day Cookout at The Plant
2025-09-01 14:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for a Labor Day Cookout on Mon, Sep 1, 2pm-6pm. The Plant has you covered for Labor Day with a fun day for the whole family. The day will feature sprinklers, lawn games, delicious craft beverages, a classic cookout menu, live music, and more!
This event takes place outdoors. 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. There is free parking. Leashed pets are allowed. This event is free. See all events at The Plant.

Live Music: Southern RanT
2025-09-01 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Southern RanT on Mon, Sep 1, 3pm-6pm. Southern RanT delivers top-shelf hits from artists like Lady A, Miranda Lambert, Little Big Town, Chris Stapleton, Lynyrd Skynyrd, and more. You can look forward to a blend of rich vocal harmonies, premium musicianship, and some straight-up fun.
There is no cover for music, but tips for the musicians are encouraged. Most events are rain or shine; if they have to cancel, they will do so as far in advance as possible. 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. There is free parking. Leashed pets are allowed. This event is free! See all events at The Plant.

Euchre Mondays at bmc
2025-09-01 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. No experience is needed. Monday is also $5 pint night at bmc brewing.
This event is free and takes place indoors. 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. Part of the Chatham County Craft Beverages & Country Inns Trail.

Fearrington Farmers Market
2025-09-02 15:00 - 17:00 | Fearrington Village, 2000 Fearrington Village Center, 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
2025-09-02 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.

Pub Trivia at Doherty's
2025-09-02 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
2025-09-02 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.

Wake Up with The Chamber
2025-09-03 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.

Music Bingo at House of Hops
2025-09-03 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.

Monthly Markets at MOSAIC
2025-09-03 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
2025-09-03 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
2025-09-03 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.

Karaoke at Hops and Berry
2025-09-03 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. 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 all events at MOSAIC. Part of the Chatham County Craft Beverages & Country Inns Trail.

Meds Instead of Meds
2025-09-04 12:00 - 13:30 | Chatham County Agriculture & Conference Center, 1192 US-64 W, Pittsboro, NC, 27312, United States
Meds Instead of Meds is a six-week series taught by Chatham County Cooperative Extension exploring the Mediterranean healthy eating style. Eating like those in the Mediterranean region has been shown to promote health and decrease the risk of many chronic diseases. The Mediterranean-style eating pattern incorporates the fundamentals of healthy eating that are traditionally practiced in countries bordering the Mediterranean Sea. The in-person series includes cooking demonstrations and taste tests!
Classes occur every Thursday, Sep 4-Oct 9, 12pm-1:30pm in the Cooperative Extension wing of the Chatham County Agriculture & Conference Center. Free parking is available at the venue.
See more events at CCACC.

Run Club at Thirsty Skull PBO
2025-09-04 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
2025-09-04 17:00 - 19:00, 2025-09-05 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
2025-09-04 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.

Summer Our State Book Club Event
2025-09-04 19:00 - 21:00 | Fearrington Barn, 500 Market Street, Pittsboro, NC, 27312, United States
Join McIntyre’s Books for the Summer Our State Book Club Event on Thu, Sep 4, 7pm-9pm. Fearrington Village is delighted to host Wiley Cash for the Our State Book Club in the Fearrington Barn with special guests, fellow North Carolinians, Georgann Eubanks, Donna Campbell, and Our State Editor in Chief Elizabeth Hudson. New York Times bestselling author Wiley Cash handpicks contemporary books by fellow North Carolinian authors and those writing books set in the state, encouraging readers to join in the fun. Wiley reviews each book in both the print and digital versions of the magazine and produces two podcast episodes highlighting the selected book and author.
Wine and hors d’oeuvres will be served. Featured books are available for sale at McIntyre’s Books at a 20% discount. Bundle your Book Club choices quarterly and receive 20% off or free freight. Tickets are $50 per person. The deadline to register is Fri, Aug 29.
Fearrington Village is part of the Chatham County Craft Beverages & Country Inns Trail. See more events at Fearrington Village.

Weekly Free Tastings at Vino!! Wine Shop
2025-09-05 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.

For Friday's Sake
2025-09-05 17:00 - 19:30 | For Garden’s Sake, 9197 Hwy 751 S, Durham, NC, 27713, United States
Need more time to shop? Well, you’re in luck because For Garden’s Sake extends its garden center hours during For Friday’s Sake, hosted on select every Friday evening in September, 5pm-7:30pm. The Potting Shed is open and serves beverages and Sunset Slush. Come and enjoy live music, food trucks, drinks, sweet treats, and the ambiance on the patio, taking in the sunset. Plus, get ready for fall by shopping seasonal items like pumpkins and mums.
Don’t forget to bring lawn chairs or a blanket for seating – patio tables go fast! Admission is free, so bring your family, friends, neighbors, and coworkers and enjoy the evening… For Friday’s Sake! Please check their calendar for the most up-to-date information on For Friday’s Sake events. The upcoming schedule of events is as follows:

Fri, Sep 5, 5pm-7:30pm Live Music with Sterling Scott
Fri, Sep 12, 5pm-7:30pm Live Music with Relay Relay
Fri, Sep 19, 5pm-7:30pm Live Music with Josh Branch
Fri, Sep 26, 5pm-7:30pm Live Music with Sterling Scott

Please note: For Garden’s Sake does not permit outside alcoholic beverages. They have a variety of drinks available at the Potting Shed. This free event takes place outdoors. Free parking is available on-site. See more events at For Garden’s Sake.

Run and Roam Fridays at The Plant
2025-09-05 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.

Moonlight Movie Series at MOSAIC
2025-09-05 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.
