Open House: An Evening at Oakland Farm
2023-08-17 16:00 - 20:00 (America/New_York) | Oakland Farm, 3355 Rosser Rd, Bear Creek, NC, 27207, United States
Join Oakland Farm for an Open House on Thu, Aug 17, 4pm-8pm! If you’re recently engaged or are wedding planning, then their summer open house is the perfect way to be inspired by some of North Carolina’s top wedding vendors. Explore their grounds and envision your wedding ceremony and reception in their open-air pavilion and air-conditioned elegant barn venue. Grab your free ticket, and enjoy a special evening with drinks, food, and all the best wedding planning tips! Stay tuned for a list of who will be attending!

American Wine Society OCL Wine Tasting
2023-08-19 15:00 - 17:00 | The Sycamore at Chatham Mills, 480 Hillsboro Street, Suite 500, Pittsboro, NC, 27312, United States
Join the American Wine Society OCL Chapter for a Wine Tasting on Sat, Aug 19, 3pm-5pm at The Sycamore at Chatham Mills. Indulge in a delightful experience of sampling and learning about a variety of Rosé wines. Whether you’re a wine enthusiast or simply enjoying a glass every now and then, this event is perfect for you!
$5 of your $25 registration goes to Chatham Animal Rescue and Education.
At this in-person gathering, you’ll have the opportunity to taste, score, and compare different Rosé wines, discovering new favorites along the way. It’s a fantastic chance to expand your wine knowledge and mingle with fellow wine lovers. Don’t miss out on this unique wine-tasting experience! If you cannot join us but want to contribute the full registration amount to CARE, then please purchase a ticket and send us an email at info@americanwinesocietyocl.org. They will make sure the full amount goes to CARE.

Downtown Pittsboro First Sunday
2023-09-03 12:00 - 16:00, 2023-10-01 12:00 - 16:00 | Pittsboro, Pittsboro, NC, 27312, United States
First Sundays, 12pm-4pm, Downtown Pittsboro First Sunday Sep 3, Oct 1, Nov 5, Dec 3
Come out and enjoy a bit of Pittsboro’s downtown charm. This family-friendly event is free to attend. Artisans, non-profits, and local businesses will be out and about as you enjoy some sweet treats, food trucks, and vendors selling art, jewelry, textiles, woodwork, soaps, pottery, and more. Just a few businesses open for Pittsboro First Sunday: Pittsboro Toys, French Connections, The Beagle, Screaming for Vintage, Oakmoss, Carolina Cravings, Circle City Books & Music, Deep River Mercantile, Marigold, Reclamation, New Horizons Downtown, Pittsboro Gallery of Arts, Chatham County Courthouse and Historical Museum, Liquidambar Gallery & Gifts, and Studio 17.
Become a vendor.

Sidewalk Chalk Festival
2023-09-09 09:00 - 12:30 | The Park at Briar Chapel, 1015 Andrews Store Rd., Pittsboro, NC, 27312, United States
Come express your creativity and create a masterpiece at the third annual Sidewalk Chalk Festival Sat, Sep 9, 9am-12:30pm at The Park at Briar Chapel. This free event organized by Chatham County Parks & Recreation is open to all artists – amateur and professional alike – to draw their chalk creations and spend the morning in the park enjoying the artwork, music, and other vendor stations. Check-in begins at 8:30am, artists will draw from 9am-11am, and awards begin at 11:30am. Artists are encouraged to preregister online, but registration will also be available on-site, on the day of the event. A tabletop drawing option is available upon request for those who are not able to draw on the ground. Open to ages 5+.

Events at the Inn at Celebrity Dairy
2023-09-17 13:30 - 16:00, 2023-10-15 13:30 - 16:00 | Celebrity Dairy, 146 Celebrity Dairy Way, Siler City, NC, 27344, United States
All events at The Inn at Celebrity Dairy.
The Inn at Celebrity Dairy is a unique GreenTravel business and bed & breakfast hosting yoga classes, Third Sunday dinners, and seasonal open barns. Visit their Eventbrite and Facebook Page to keep up-to-date on the latest events and offerings.
Third Sunday Dinners, 1:30pm-4pm Sep 17, Oct 15, Nov 19

Third Sunday dinners are always a fun afternoon featuring a four or five-course meal with hyper-local ingredients prepared by Celebrity Dairy’s in-house chefs. Plus, there will be a lot of Celebrity Dairy cheeses for you to enjoy! Each month features a menu created with a specific theme in mind, focusing on what is available during that season.

The dinners also include a tour of the barns where you will get to meet the Celebrity Dairy goats and learn about them and how they’re raised. They love visitors and will be sure to greet you as you enter the barns! Please feel free to bring a bottle of wine with you to complement the meal.

2nd Annual Pittsboro Treasure Quest
2023-09-30 09:30 - 15:00 | Pittsboro, Pittsboro, NC, 27312, United States
Join Circle City Merchants for the 2nd Annual Pittsboro Treasure Quest Sat, Sep 30, 9:30am-3pm. This event is a scavenger hunt that will take your team through challenges and adventures in and around downtown Pittsboro.
Teams of 2 to 6 people will move through Pittsboro businesses, completing challenges and accruing points. The cost to participate is $45 per team. Check-in is from 9:30am-10:45am at Havoc Brewing Company. Breakfast, coffee, and juice will be provided for participants from local restaurants. Upon sign-in, each team will receive a swag bag with coupons from local businesses, snacks, and their first clue. Teams who accrue the most points for challenges completed will win big prizes!
1st place wins $500, 2nd wins $300, and 3rd wins $200. There are also great prize baskets for Unique Team Name, Most Enthusiastic/Team Spirit, and Best Costumes, so get those creative juices flowing! Extra points will also be awarded to the first 5 teams to register, so sign up early.
Water stations will be sprinkled throughout the event route, so be sure to stay hydrated. Chatham Transit will be shuttling teams to Pittsboro West locations, The Plant, and Downtown Pittsboro, so park that car and leave the driving to us! Email circlecitymerchants@gmail.com with questions!

Sixteenth Annual PepperFest
2023-10-01 15:00 - 18:00 | The Plant, 220 Lorax Lane, Pittsboro, NC, 27312, United States
Abundance NC presents The Sweet Sixteenth Annual PepperFest, Sun, Oct 1, 3pm-6pm! PepperFest is a celebration of sustainable agriculture, local farmers, and the creativity of the Piedmont’s top chefs, brewers, and artisans. They are back at The Plant to host folks who enjoy live music and revelry, learning, and discovery – including a kid’s craft and fun zone – while filling up on delicious pepper-themed dishes made with delicious, locally grown sweet, hot, and smoky NC peppers.
Chefs compete for awards. Foodies taste all the different dishes made from peppers grown in the Piedmont of North Carolina. Children run wild, folks dance, laugh, and enjoy the many different creations. A Pepper Queen and King are crowned, local businesses and nonprofits share their news, and they all go home very happy. They will have live music with Soultriii, an artistic educational, and cultural walkthrough, a 21+ lounge, a kid’s zone, vendors, and fun for the entire family! Get your tickets today! Prices will go up over the coming months.

Events at Thirsty Skull Brewing - Pittsboro
2023-10-05 16:00 - 18:00, 2023-10-12 16:00 - 18:00, 2023-10-14 15:00 - 18:00, 2023-10-19 16:00 - 18:00, 2023-10-26 16:00 - 18:00 | Thirsty Skull Brewing – Pittsboro, 684 West Street, Pittsboro, NC, 27312, United States
All events at Thirsty Skull Brewing – Pittsboro. Pittsboro taproom and biergarden hosting karaoke nights, run clubs, and more. Special deals include 1/2 price crowlers on Wednesdays and $4 pours all day long on Thirsty Thursdays.
Check out their Facebook Page for updates on new brews and batches, local food trucks, and occasional live music. Part of Chatham County’s Craft Beverages & Country Inns Trail.
Sat, Oct 14, 12pm-9pm Fest Yourself Oktoberfest
Come out and celebrate beer in its original fashion! Decorations, live music from 3pm-6pm, traditional German food served up at 4pm, games, Stien holding competition, best costume, and more!
Weekly Events
Thursdays, 5pm-7pm: Run Club
Come out to the running track for 20% off your tab for the night when you walk or run.
First Friday of the Month, 7pm-9pm: Karaoke with JV Jams
Jam out to your favorite songs with friends and family.

House of Hops Events
2023-10-05 19:00 - 21:00, 2023-10-11 18:00 - 20:00, 2023-10-18 18:00 - 20:00, 2023-10-21 12:00 - 22:00, 2023-10-25 18:00 - 20:00 | House of Hops, 112 Russet Run, Pittsboro, NC, 27312, United States
All events at House of Hops in Pittsboro. The Pittsboro location of this local bottle shop hosts a run club, local food trucks, bingo, trivia nights, special releases, and more! Deals include $5 off pints and glasses of wine, and 20% off wine bottles every Monday.
Check out the House of Hops Facebook page for other weekly deals and promotions, new additions to their draft list, and special events. Part of Chatham County’s Craft Beverages and Country Inns Trail.
Sat, Oct 21, 12pm-10pm Halloween Fall Festival
Save the date! Join House of Hops for fall fun, including activities for the kiddos, seasonal beers on tap, live music with GLK, and more. Costumes welcome!
Weekly Events
Tuesdays, 5pm-7pm: Run Club
All skill levels welcome, 3-5 mile routes available. Special deals are available for House of Hops Run Club members, including $5 pints after every run. Visit their website for directions on how to sign up for a membership. The bottle shop also offers 20% off mix-and-match six packs every Tuesday (for everyone, Run Club member or not).
Wednesdays, 6pm-8pm: Music Bingo Show
Enjoy singing and dancing during this family and pet-friendly free game – plus a chance to win fun prizes! Bring your own food or order from nearby local restaurants. Also, save 25% on growlers every Wednesday.
Thursdays, 7pm-9pm: OpinionNation
Test your knowledge and team up with your friends and family for OpinionNation, a survey-based, Family Feud-style game, with winners walking away with House of Hops gift cards.

Quiltmaker Cafe Fall Festival Fundraiser
2023-10-06 17:00 - 19:00 | Huckleberry Trail Farm, 143 Pleasant Hill Church Rd, Siler City, NC, 27344, United States
Join Quiltmaker Cafe for their Fall Festival Fundraiser Fri, Oct 6, 5pm-7pm at Huckleberry Trail Farm, and enjoy a delightful evening filled with live music, delectable snacks and desserts, games, a corn maze, face painting, and an exclusive silent auction, all in support of a worthy cause. By attending the Fall Festival Fundraiser, you are contributing to a worthy cause. All funds raised will directly support The Quiltmaker Cafe’s initiatives, making a positive impact on our community. Your presence and support are greatly appreciated!
Quench your thirst with a one-of-a-kind QuiltSquare brew created by bmc brewing or award-winning wine from FireClay Cellars. Adults ages 21 and up receive two free drink tickets with the purchase of admission. Enjoy food from Carolina Cravings and The Travelling Cafe.
Get ready to tap your feet and groove to the lively tunes of local musicians as they set the stage ablaze with their performances. The soothing sounds of acoustic melodies and foot-tapping beats will create a magical ambiance throughout the event. Bring out your competitive spirit and engage in various entertaining games and activities. From classic carnival games to engaging fall-themed challenges, there’s no shortage of fun and laughter for attendees of all ages.

Take part in our exclusive silent auction featuring a variety of coveted items and experiences. Bid on remarkable prizes donated by generous supporters and local businesses, knowing that every winning bid goes directly to supporting the cause. Silent Auction Items include donations by Perch Coworking.

Events at Thirsty Skull Brewing - Siler City
2023-10-06 19:00 - 21:00, 2023-10-10 19:00 - 21:00, 2023-10-17 19:00 - 21:00, 2023-10-24 19:00 - 21:00, 2023-10-31 19:00 - 21:00 | Thirsty Skull Brewing, 915 N Second Ave, Siler City, NC, 27344, United States
All events at Thirsty Skull Brewing – Siler City.
Small scale brewery offering game nights, local food trucks, and occasional live music. Stop by for $4 pours on Wednesdays and half-off all 32oz. cans to-go every Sunday.
Check out their Facebook page for updates on new brews and batches, deals, and special events.
Fri, Nov 10, 6pm-9pm Ivan Vest
Weekly Events
Tuesdays, 7pm-9pm: Wii Sports
Be sure to bring your wrist straps! Hosted every Tuesday starting at 7pm, sign-up ends at 6:30pm.
Fridays, 7pm-9pm: Music Bingo
Grab a pint, hang out, and enjoy some music bingo!

Chatham County Agriculture & Conference Center Events
2023-10-20 14:00 - 22:00, 2023-10-21 10:00 - 22:00, 2023-10-22 10:00 - 17:00 | Chatham County Agriculture & Conference Center, 1192 US-64 W, Pittsboro, NC, 27312, United States
All events at the Chatham County Agriculture & Conference Center.
The Chatham County Agriculture & Conference Center (CCACC) is Chatham County’s largest multipurpose venue, with an exhibit hall, lobby, four meeting rooms, and outdoor vendor space. Their team puts a premium on good customer service. CCACC serves a variety of clients and balances revenue-generating events with community needs through its rate structure. The primary use of the space is reflected in the year-round meetings and workshops to meet the agricultural and educational programming needs, a significant part of CCACC. The conference center offers state-of-the-art A/V technology, including a live streaming package.
Upcoming Chatham County Agriculture & Conference Center Events
Fri, Oct 20, 2pm-10pm; Sat, Oct 21, 10am-10pm; and Sun, Oct 22, 10am-5pm Ancient Arts Festival
Fri, Dec 1, 9am-11:30am Fundamentals of Composting

Downtown Pittsboro Reclamation Vintage Market
2023-10-22 12:00 - 16:00 | Reclamation, 102 Hillsboro St, Pittsboro, NC, 27312, United States
Reclamation invites you to a Downtown Pittsboro Vintage Market on Sun, Oct 22 from 12pm-4pm. Come out for a unique outdoor vintage and artisan market with beverages, a food truck, and an eclectic mix of some of the best vintage vendors around. This family-friendly event is free. Please park in public parking spaces only, parking near the store will be limited. Look for the “Market” signs.

The Parlour Open House Tours
2023-10-26 17:00 - 19:00 | The Parlour at Manns Chapel, 175 Poythress Road, Chapel Hill, NC, 27516, United States
At this casual Open House Tour on Thu, Oct 26, 5pm-7pm, The Parlour at Manns Chapel will open its doors and offer guided tours for those interested in booking their venue for any event you may be planning (wedding, celebrations, corporate, etc.). Or, forego the guided tour and stroll about on your own taking in all The Parlour has to offer! Light the fire and relax.
Enjoy light refreshments while touring alone or guided, and see this award-winning venue where “Love Big, Celebrate Small” is the perfect way to gather. Kindly register to let them know that you will be joining them. Private tours are available through their website if you can’t make the open house.
The Parlour at Manns Chapel is the only venue created for the refined, intimate event experience. If you don’t believe in obligatory invites, and you value knowing everyone at the table – they’re with you. If you prefer styled, more creative details over an “audience,” then celebrate small with them at The Parlour, where “small” means well-curated, discerning, and the mark of meaningfulness.
