The Street Fair Took Halloween Saturday, So Pittsboro's Costumes Start Friday

Last year the Rotary Club of Pittsboro held its Street Fair on October 25. This year it falls on Saturday, October 31. That puts more than 100 vendors, food trucks, live music and the annual Trike Race on Hanks, Fayetteville and Salisbury streets from 10 a.m. to 6 p.m. on Halloween itself.

Those eight hours sit in the middle of the weekend. Pittsboro's other posted Halloween events fall around them. One is the evening before, out at MOSAIC. One is Saturday morning on NC 87. One starts an hour after the fair's vendors close. The weekend ends Sunday afternoon on West Salisbury Street. If you're in Pittsboro, Halloween this year runs from Friday evening through Sunday afternoon.

The week starts at The Mod

The Mod gets the week going downtown. Its calendar has Peak City Band on Sunday, October 25, from 7 to 10 p.m., then Karaoke with JVJams, Halloween Edition, on Wednesday, October 28, also 7 to 10 p.m. Its calendar has nothing on October 31.

These dates come during a change at The Mod. According to Chatham Magazine, the restaurant side closed temporarily in August while owner Jamie Ellen renovates the bar into a more intimate dinner space. The same September 18 piece describes a weeknight lineup that includes shag dancing, pool and poker leagues, salsa lessons and all-ages Thursday blues jams. We couldn't find anything published that says the restaurant side has reopened, so check The Mod's own channels before you plan dinner around it.

Friday, October 30: the trunk-or-treat moves to MOSAIC

Because the fair takes Saturday daytime downtown, Pittsboro's big trunk-or-treat happens Friday night. MOSAIC at Chatham Park is pairing its Moonlight Movie Series screening of Hocus Pocus 2 with a trunk-or-treat on October 30. The lot opens and trick-or-treating starts at 6 p.m. The movie starts at 7, and the event wraps at 9. MOSAIC's October calendar has nothing on the 31st, so its Halloween program comes the night before the Street Fair and doesn't compete with it.

It's free, but you need tickets, which are handled through Eventeny. The event page lists a few rules worth knowing before you load the car:

• The venue is the open parking lot next to Greek Kouzina. From US 501, turn onto Russet Run, take the third exit at the roundabout and head toward the new Hampton Inn.
• Bring a lawn chair or blanket. Pets are welcome.
• Expect bag checks and security screening at the entrance.
• You can't bring in food or drinks bought outside MOSAIC. If you buy from a MOSAIC business, show your receipt to event security. Food and drinks are also sold on site.

The receipt rule makes it easy to pick up dinner at a MOSAIC restaurant on the way in. Plan that stop around what's open now, though. Chatham Magazine notes that Cafe Root Cellar at MOSAIC closed on September 19, 2026.

Saturday, October 31: three shifts in three places

Saturday has three shifts. The Refuge's tour falls inside the fair's hours, and Vino!!'s party starts after the fair closes.

Morning on NC 87. Piedmont Farm Animal Refuge runs its Halloween tour from 11 a.m. to 2 p.m., with vegan trick-or-treating, face painting and pumpkin activities. Family-friendly costumes are welcome. The fair runs before, during and after the Refuge's window, so a family can do the tour and still catch the fair on either side of it.

Daytime downtown. According to the Rotary Club of Pittsboro, the fair goes ahead rain or shine and admission is free. Proceeds support Rotary's community programs, including scholarships, CORA's Turkey Tuesday, Meals on Wheels and Books for Every Reader. The fair's posted highlights don't mention costumes or a Halloween theme. Any costumes on the street will be visitors' own choice, not part of the program.

For getting there, the Rotary page lists a free shuttle from Central Carolina Community College. We couldn't find a 2026 shuttle timetable, parking map or street-closure schedule. The parking guidance going around online is from 2025, so for this year's plan, treat the CCCC shuttle as the one confirmed option.

The hour between. The vendors close at 6 p.m., and Vino!! opens its party at 7. That leaves an hour for dinner. Tikka Masala Indian Grill at 440 East St. serves dinner on weekends from 4 to 8:30 p.m. It moved from the food truck that started in Apex into its own building, opening for takeout in November 2025 and adding dine-in service in January.

Night on Hillsboro Street. Vino!! Wine Shop calls this its second Halloween party. It has a costume contest and spooky Halloween cocktails, and the shop stays open until 10 p.m. under the tagline "Trick or treat with wine!!" Of everything posted for October 31, it's the only adult costume event, and it starts after the fair has packed up.

A lunch counter on Salisbury Street is open all three days

Salisbury Street is one of the fair's three blocks, and The Quiltmaker Cafe sits on it at 75 W. Salisbury St. After five years of mobile pop-ups, the nonprofit opened its permanent home there this past May. Chatham Magazine readers voted it one of the Best New Businesses in the 2026 Best of Chatham poll.

The menu has no prices. Guests pay what they can, donate produce or eggs, or volunteer before or after their meal. Volunteers run food to tables, make coffee and tea, bus tables and wash dishes. The counter serves hot deli sandwiches, soup, salad, brunch items like frittatas and waffles, and desserts, some baked in-house and some from Carolina Cravings Co.

The cafe is open Sunday, Monday, Tuesday, Friday and Saturday from 11 a.m. to 2 p.m. That means it's open every day of Halloween weekend: before the drive to MOSAIC on Friday, in the middle of the fair on Saturday, and right up to the start of First Sunday. Volunteering a shift is the cafe's posted way to contribute without cash. Fair weekend brings one of downtown's biggest crowds of the year to its block.

Sunday, November 1: back to West Salisbury

The weekend ends a short way down the same street. The Pittsboro Business Association lists First Sunday for November 1 from noon to 4 p.m. at the Downtown Pittsboro Pop-Up Park, 50 W. Salisbury St., with live music, food trucks and artisan vendors. The visitors bureau also lists it for noon to 4 p.m.

This year First Sunday comes the day after the Street Fair, on the same blocks, so downtown hosts outdoor vendor markets two days running. First Sunday runs on the first Sunday of each month from April through December, so after November 1 the only date left this year is December 6.

The weekend at a glance

1. Sunday, Oct. 25, 7 to 10 p.m. Peak City Band, The Mod
2. Wednesday, Oct. 28, 7 to 10 p.m. Karaoke with JVJams, Halloween Edition, The Mod
3. Friday, Oct. 30, 6 to 9 p.m. Hocus Pocus 2 and trunk-or-treat, MOSAIC lot next to Greek Kouzina
4. Saturday, Oct. 31, 10 a.m. to 6 p.m. Pittsboro Street Fair, with the Trike Race from noon to 3
5. Saturday, Oct. 31, 11 a.m. to 2 p.m. Halloween Tour & Explore, Piedmont Farm Animal Refuge
6. Saturday, Oct. 31, 7 to 10 p.m. Halloween Party, Vino!! Wine Shop
7. Sunday, Nov. 1, noon to 4 p.m. First Sunday Pittsboro, Pop-Up Park at 50 W. Salisbury St.

For the summer version of this calendar, see our look at how Pittsboro's summer split between downtown and MOSAIC. The weekend above follows the same pattern, with MOSAIC hosting Friday and downtown hosting Saturday and Sunday.

At Crumpler Realty Group, we follow Pittsboro's calendar the same way we follow its market, one block and one weekend at a time. If the Street Fair has you wondering what your home near Hanks or Salisbury Street is worth, you can request a home valuation or book a free consultation, and we'll go through the numbers with you.