Pittsboro-Siler City Convention & Visitors Bureau

Music at Roost Beer Garden
2025-09-04 17:00 - 19:00, 2025-09-05 17:00 - 19:00 (America/New_York) | 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.

Live Piano Music at The Sycamore
2025-09-04 18:00 - 21:00, 2025-09-05 18:00 - 21:00, 2025-09-06 18:00 - 21:00, 2025-09-09 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.

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.

Come Out and Play Sculpture Show
2025-09-06 12:00 - 20:00 | JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312, United States
Dozens of artists, creating in a myriad of media, are represented in this annual Come Out and Play Sculpture Show, now in its 24th year. The event takes place on a 17-acre homestead and is a gift from hosts to guests and artists. Artists do not pay a participation fee and keep all proceeds from their sales (many of the works on display are for sale). There are some out-of-state artists, but most are local to North Carolina. Each reception is filled with fantastic art and local vendors, free food and drink from the artists and hosts, visits with the horses and pigs, and live music from the North Carolina Songwriters Co-op.
The opening reception for 2025 is Sat, Aug 23 and Sun, Aug 24, 12pm until dark. Additional receptions are hosted on the following Saturdays: Aug 30, Sep 6, Sep 13, and Sep 20, 12pm until dark. Events are free. This event is family-friendly and pet-friendly (please keep all dogs on a leash). For more information, contact Debbie Meyer at writetoeloise@gmail.com or 919.357.6142.
DIRECTIONS AND PARKING
Location: JimGin Farm, 150 Wild Horse Run, Pittsboro, NC, 27312.
Find Your Way With #w3w: ///lizard.exhausting.profuse.
Parking Directions: Come down Wild Horse Run to the end. Please do not park on this road. On the right-hand side, go through the wooden gates and park on the right lawn. In the event that the right lawn is full, folds will be there to guide you to parking on the left. There is plenty of parking, so please follow their guidance and do not block any roads going in or out.
ACCESSIBILITY INFORMATION
The farm is not paved but there are gravel and grass areas. Parts of the property can be navigated with care for those with walkers or wheelchairs, including the outdoor area where tents are set up and where the musicians perform. Many individuals with walkers and wheelchairs, including the artists themselves, attend the event every year. Please contact the event organizer for additional accessibility questions.

THE HISTORY BEHIND THE EVENT
The Come Out and Play Sculpture Show began in 2002 to commemorate the first anniversary of 9/11 and has continued since then to promote kindness in the world through art and by connecting people. Debbie Meyer and her husband, Eric Brantley, coordinate and host this amazing show each year; it is truly a rewarding gift!

Football Season Kickoff at House of Hops
2025-09-06 13:00 - 22:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Football season is right around the corner, and House of Hops is celebrating kickoff day with an all-day celebration. The day starts with House of Hops’ first-ever Chicken Wing Cookoff, hosted Sat, Sep 6, 1pm-3pm. You can cook wings at home or on-site. Prizes go to the top three wings and the best flavor (rub or sauce). Then they will start their Cornhole Tournament at 4pm. Prizes go to the top three finishers here as well. To conclude the evening, they will host a Watch Party for UNC’s first road game of the season at 7pm. Free pizza will be available to accompany their tasty tap list. Plus, they’re expecting a special surprise guest!
If you’re interested in joining the Cookoff, Cornhone, or both, send House of Hops a DM, leave a comment on their Facebook Page, sign up in the shop, or send an email to evan@houseofhopsnc.com. More events at House of Hops. Part of the Chatham County Craft Beverages & Country Inns Trail.

Carolina Brewery Fall Music Series
2025-09-06 17:30 - 20:00 | Carolina Brewery & Grill, 120 Lowes Dr, Ste 100, Pittsboro, NC 27312, NC, 27312, United States
Take in live music from local musicians on the patio at Carolina Brewery and Grill during their Fall Music Series. Hosted Saturdays, September-October, 5:30pm-8pm. See specific dates and performers listed below.

Sat, Sep 6, 5:30pm-8pm Deep Chatham Ramblers.
Sat, Sep 13, 5:30pm-8pm ZamBamBoogee.
Sat, Sep 20, 5:30pm-8pm Vinnie’s Garage Band.
Sat, Sep 27, 5:30pm-8pm The 8:59’s.
Sat, Oct 4, 5:30pm-8pm Mondo Guitaro.
Sat, Oct 11, 5:30pm-8pm Big T.
Sat, Oct 18, 5:30pm-8pm Jason Damico.
Sat, Oct 25, 5:30pm-8pm Colby Jack and The High Lifes.

Admission is free. Enjoy burgers, tacos, apps, and of course, their award-winning beer. Their Oktoberfest Menu is available Tue, Sep 16-Tue, Sep 30. Part of the Chatham County Craft Beverages and Country Inns Trail. See all events at Carolina Brewery & Grill.

The Wanderer's Market
2025-09-07 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.

Live Music: Colby Jack and The High Lifes
2025-09-07 15:00 - 17:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Colby Jack and The High Lifes on Sun, Sep 7, 3pm-5pm. Colby Jack & the High Lifes are a high-energy Vintage Honky Tonk band from Greensboro, North Carolina. Playing all your country favorites from Hank Williams to Travis Tritt, as well as their timeless originals. Grab a beer and a dance partner!
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.

Pittsboro End-of-Summer Fest
2025-09-07 16:00 - 20:00 | Pittsboro Pop-Up Park, West Salisbury Street, Pittsboro, North Carolina, 27312, United States
After rescheduling their annual summer celebration due to inclement weather, The Pittsboro Business Association proudly presents Pittsboro End-of-Summer Fest on Sun, Sep 7, 4pm-8pm. Enjoy all the usual Summer Fest activities, but in (hopefully) cooler temperatures. Activities typically include a Decorated Bicycle Parade, juggling, giant balloons, hula hooping, balloon animals, a duck pond for prizes, axe throwing, and fun for the whole family. There will also be food trucks and local vendors. Enjoy live music from SouLe and the Super Band and Your Mama’s New Boyfriend.
This celebration takes place at the Pittsboro Pop-Up park between Salisbury and Hanks streets in downtown Pittsboro. This venue is wheelchair accessible. Leashed pets are allowed, but discouraged.
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! Summerfest is sponsored by the Pittsboro Business Association, and the Chatham County History Association is a proud participant.

A Night of Giving: Vidas de Esperanza Fundraiser
2025-09-07 18:30 - 20:30 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Join Vino!! Wine Shop for A Night of Giving: Vidas de Esperanza Fundraiser on Sun, Sep 7, 6:30pm-8:30pm.
Many of you may not know, but Vino!! is very dedicated to the non-profit, Vidas de Esperanza (they donate Wine Fest proceeds to the cause). Vidas is dedicated to enhancing the lives of Chatham County residents by increasing access to education, technology, and healthcare. In particular, Vidas runs a free dental and medical clinic on the last Saturday of every month in Siler City. Anna’s father, a physician at UNC for 50 years, works at the clinic and got UNC Hospitals involved – they now send physicians and dentists to work at the clinic monthly. This is an entirely non-profit organization – 100% of any funds received go directly to the mission. No doctors or owners receive any payment.
To generate funds for Vidas, Vino!! is hosting this night of giving. The cost is $150 per person and includes an evening of connection and fun during a wine tasting experience, featuring a curated selection of high-end wines, light bites, and a heartfelt mission. The food and wine lineup is TBA.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

Euchre Mondays at bmc
2025-09-08 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.

79 West Breakfast Club
2025-09-09 09:00 - 10:30 | 79° West, 120 Mosaic Blvd, Suite 120, Pittsboro, NC, 27312, United States
Welcome to the 79°West Monthly Breakfast Club – their laid-back take on the traditional morning networking event, hosted on the first Tuesday of every month, 9am-10:30am. This free event features a new guest speaker every month, plus:

Live acoustic music.
Tasty breakfast treats.
Giveaways and complimentary coworking until 5pm.
Local news from Gene Galin of the Chatham Journal.
Industry insights from Breakfast Club Sponsors.

This FREE indoor event is open to coworking members and the public. Part of MOSAIC at Chatham Park. See all events at MOSAIC.

Fearrington Farmers Market
2025-09-09 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
2025-09-09 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
2025-09-09 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
2025-09-09 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
2025-09-10 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. Fair Game Beverage Company is part of the Chatham County Craft Beverages & Country Inns Trail.

Music Bingo at House of Hops
2025-09-10 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.

Open Mic Nights at NC Arts Incubator
2025-09-10 18:00 - 20:00 | NC Arts Incubator, 223 N Chatham Ave, Siler City, NC, 27344, United States
Join the NC Arts Incubator for Open Mic Nights hosted every second Wednesday, 6pm-8pm. Music, poetry, and spoken-word works are encouraged. Sign-up opens at 5:30pm. Next door, The Chatham Rabbit will be open and selling coffee.
See more events hosted by the NC Arts Incubator.

Jazz Nights at The Sycamore
2025-09-10 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
2025-09-10 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.
