Blues Jam at The MOD
2025-12-25 19:00 - 22:00, 2026-01-01 19:00 - 22:00 (America/New_York) | 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.

Live Music at The Plant: Qwister
2025-12-26 17:00 - 20:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Join The Plant for Live Music with Qwister on Fri, Dec 26, 5pm-8pm. Ryan Melquist, also known as “Qwister,” is a full-time touring musician with 12 years of experience. His sound blends reggae, pop, country, folk, jam, and party rock influences. Ryan puts his own twist on well-known covers from across the decades — turning them into upbeat reggae-rock medleys that get the crowd moving.
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.
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.

Run and Roam Fridays at The Plant
2025-12-26 17:00 - 21:00, 2026-01-02 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
2025-12-26 18:00 - 21:00, 2025-12-27 18:00 - 21:00, 2025-12-30 18:00 - 21:00, 2026-01-06 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.

Live Music: Jason Damico
2025-12-27 19:30 - 22:30 | Hops & Berry, 120 Mosaic Blvd, Suite 100, Pittsboro, NC, 27312, United States
Come out to Hops and Berry-Pittsboro for Live Music with Jason Damico. Performances take place on the following dates:

Sat, Jun 7, 7:30pm-10:30pm.
Sat, Aug 23, 7:30pm-10:30pm.
Sat, Oct 25, 7:30pm-10:30pm.
Sat, Dec 27, 7:30pm-10:30pm.

This event is free and takes place indoors. There is no cover for entry, but tips for the musicians are encouraged. 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.

Songwriter Open Mic at bmc
2025-12-28 14:00 - 17:00 | bmc brewing, 213 Lorax Lane, Pittsboro, NC, 27312, United States
On the fourth Sunday of every month, 2pm-5pm, bmc brewing hosts a Songwriter Open Mic Night with Michael J. Brennan. Explore the unique acoustics in the halls of bmc brewing! No drums kits, no backing tracks – just songwriters sharing their best covers and originals.
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.

Euchre Mondays at bmc
2025-12-29 18:00 - 20:00, 2026-01-05 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.

Paint and Pint Night at House of Hops
2025-12-29 18:30 - 20:30 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
Join House of Hops for a Paint and Pint Night on Mon, Dec 29, 6:30pm-8:30pm. Come cozy up at House of Hops while Wine & Design guides you through a step-by-step instructed paint class on pre-sketched canvases.
Tickets are $25 per person. No experience required. Arrive 30 minutes early to order your drinks! Wine & Design will have everything ready for you to create your very own masterpiece. The event is NOT BYOB; discounts and coupons are not valid. Email chapelhill@wineanddesign.com with any questions!!
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.
CANCELLATION POLICY
All sales are final; no refunds will be issued if a customer cancels their reservation. To receive a credit, the customer must email chapelhill@wineanddesign.com 24 hours before the event. Please note that if you book a reservation within 24 hours of the class, you will not receive a credit if you cannot attend. If there is a threat of inclement weather or the event has low attendance, it may be cancelled. If this is the case, you will be given credit for another class of equal value.

Run Club at House of Hops
2025-12-30 18:00 - 20:00, 2026-01-06 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
2025-12-30 19:00 - 21:00, 2026-01-06 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. 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.

Pub Trivia at Doherty's
2025-12-30 19:00 - 21:00, 2026-01-06 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.

New Year's Eve Party at Doherty's
2025-12-31 16:30 - 21:00 | Doherty’s Irish Pub and Restaurant, 56 Sanford Road, Pittsboro, NC, 27312, United States
Join Doherty’s Irish Pub & Restaurant for an unforgettable New Year’s Eve Dinner and Party on Wed, Dec 31, 4:30pm-9pm. Get there early and enjoy any of their menu favorites, or indulge in Chef’s Specials for the evening (listed below). Plus, live music from Two Times Around starts at 6pm. There will be an Irish New Year Toast at 7pm EST (12am GMT). Come ring in the New Year with friends and family! Dinner reservations are available online.
CHEF’S SPECIALS

Smoked Pork Belly Bruschetta.
Prime Rib with a Merlot Demi-Glaze.
Lobster Pot Pie.
Sticky Toffee Pudding.

This event takes place indoors. Doherty’s first floor is wheelchair accessible and offers accessible seating. Free public parking is available just across the street. Leashed pets on the patio only, please. See more events at Doherty’s Irish Pub & Restaurant.

New Year's Eve Party at Vino!!
2025-12-31 17:00 - 19:00 | Vino!! Wine Shop, 89 Hillsboro Street, Suite A, Pittsboro, NC, 27312, United States
Kick off 2026 on the right foot with a New Year’s Eve Party at Vino!! Wine Shop on Wed, Dec 31, 5pm-7pm. Celebrate the end of the year with bubbly, as well as food packages available for purchase. This event takes place indoors.
All tastings and events at Vino!! Wine Shop. Part of Chatham County’s Craft Beverages and Country Inns Trail.

A Roving New Year's Eve!
2025-12-31 18:00 - 2026-01-01 00:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Welcome 2026 with A Roving New Year’s Eve at The Plant, Wed, Dec 31, 6pm-Thu, Jan 1, 12am. Join The Plant on New Year’s Eve for “one last crawl” to end 2025! Fair Game Beverage Company, bmc brewing, Starrlight Mead, and Koshu Sake will have festive beverages and creative spirit cocktails, specials, and, of course, sparkling wine by the bottle and glass. Kingston 99 Kitchen and Ta Contento will be open for dinner. There will be fire pits, an intention table, a dance party under the disco ball, and an hourly Apple Drop starting at 8pm and continuing until midnight to ring in 2026. Bring your friends and family- they’ve got something for everyone!
There is no cover fee for this free public event, and parking is free. Private tables and bottle service are available for a fee. Dress code is casual attire. The event takes place indoors and outdoors at The Plant. Leashed, well-behaved pets are allowed outside; pet policies may vary by individual business. 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. See all events at The Plant. Part of the Chatham County Craft Beverages & Country Inns Trail.

Irish New Year at City Tap
2025-12-31 18:30 - 22:00 | City Tap, 89 Hillsboro Street, Suite B, Pittsboro, NC, 27312, United States
If you don’t like staying up until midnight, come celebrate an Irish New Year at City Tap on Wed, Dec 31, 6:30pm-10pm. The countdown will begin at 7pm EST (Dublin’s midnight). There will be live music from Trash Van Fever starting at 7pm as well! Enjoy a champagne toast and rocking tunes!
This event takes place at The City Tap. The patio is wheelchair-accessible from the back of the building. There is a lift to the second floor, and the service area is located on the secondary staircase that connects to the patio. See all events at City Tap.

Karaoke at Hops and Berry
2025-12-31 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.

Quiltmaker's Annual New Year's Open House
2026-01-01 13:00 - 16:00 | Quiltmaker Cafe, 75 W Salisbury St, Pittsboro, NC, 27312, United States
Join your community members and Quiltmaker Cafe for their Annual New Year’s Open House on Thu, Jan 1pm-4pm. Start 2026 right with desserts, games, and community at Quiltmaker’s future home (opening soon). This celebration is an Open-House, child-friendly event, so please stay for as long as you are able. Volunteer opportunities are available. Participating businesses include Circle City Ice Cream and bmc brewing.
No registration is required. Free parking is available on the street and in the public lot across the road. The space is ADA-compliant. No pets allowed.

Run Club at Thirsty Skull PBO
2026-01-01 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
2026-01-01 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.

Music Bingo at House of Hops
2026-01-07 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
2026-01-07 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.
