The Ultimate Orange County and Chatham County Checklist

Everything a local should do, plus seasonal favorites

kids with ice cream on a truck
Carleigh Cotten and her brother, Titus Cotten, enjoy a milkshake and an ice-cream cone from S&T’s Soda Shoppe outside Circle City Books & Music, both “just off the circle” in Pittsboro.

Photography by John Michael Simpson

1 Grab an ice cream from S&T’s Soda Shoppe and stroll along Hillsboro Street

2 Find your new favorite vintage tee, bespoke candle or retro home decor at Marigold, Little Boho Valley or Screaming for Vintage in Pittsboro

3 Watch a movie at the historical Varsity Theatre

4 Jam with live, local bands at Nash Street Tavern or Hot Tin Roof in Hillsborough or The City Tap in Pittsboro

5 Finish a blue cup at He’s Not Here

6 Visit Chapel Hill’s most perfect sunset spot – Merritt’s Pasture

7 Nibble on a nutty fruitcake at Southern Supreme Fruitcake & More

8 Rush Franklin Street after a UNC victory over Duke

9 Groove to a favorite band at Cat’s Cradle or catch an up-and-coming hip-hop artist at Local 506

10 See the Belted Galloway cows and stroll the walkable Fearrington Village

11 Go antiquing at Countryside Collectibles Antique Mall or check out refinished furniture at Gathered Home Decor

12 Catch an independent film at the Chelsea Theater

13 Learn about the history of Tar Heel hoops at the Carolina Basketball Museum

14 Better yet, cheer on UNC during a game at the Dean E. Smith Center or watch it at Four Corners

15 Choose among different tasty salsas at Carrburritos

16 Try a Bell Tower Blueberry Wheat beer at Top of the Hill

17 Drink from the Old Well

18 Play a round of golf at the newly renovated UNC Finley Golf Course

19 Release some steam by ax-throwing at Chatham Axes

20 Use your Italian dinnerware purchased at the VIETRI outlet store in Hillsborough

21 Enjoy the latest exhibition at the Ackland Art Museum or stroll through the artist-owned FRANK Gallery in Carrboro

22 Get local produce from the Carrboro Farmers Market, the Chapel Hill Farmers Market, the Eno River Farmers Market, the Fearrington Farmers Market, the Pittsboro Farmers Market or the Chatham Mills Farmers Market

23 Take a nature walk at the North Carolina Botanical Garden

24 Beat your friends in a round of pool at Zog’s Art Bar & Pool Hall or play your favorite old-school arcade game at The Baxter

actors perform on stage
The cast and crew of the Prime Time Players put on three performances of “Chinese American Wedding” at the Seymour and Passmore centers.

25 Enjoy a pickup game of mahjong or pingpong, take a Zumba class or watch a performance at the Seymour Center

26 Stroll on one of our many beautiful greenways, like the Tanyard Branch Trail, where metalwork art is on display by local artist Leo Gaev

27 Go on a burger tour with stops at Johnson’s Drive-In in Siler City and Buns and Al’s Burger Shack in Chapel Hil

28 Satisfy your sweet tooth with a slice of cake at Nantucket Grill or a creative confection at Glasshalfull

29 Pick up a six-pack at Beer Study or The Casual Pint

30 See a Carolina Performing Arts show at CURRENT ArtSpace + Studio or Memorial Hall

31 Greet the UNC football team and cheerleaders as they make their way to Kenan Stadium during the pregame Victory Walk

32 Relax on the lawn of Weaver Street Market in Carrboro

33 Order a coffee and a treat at The Chatham Rabbit in Siler City or at
Aromatic Roasters in Pittsboro

34 Head to Chatham Park‘s Penguin Place for a beer from House of Hops, a sandwich at Café Root Cellar and some freshly made guacamole at Mi Cancun

35 Order a single, double, or, if you dare, a triple BLT at Merritt’s Grill

36 Buy a cut of meat from Cliff’s Meat Market

two guys with burgers
College classmates Charlie Farris and Jason Kesler bought iconic hamburger eatery Al’s Burger Shack in 2022, taking over both the location on West Franklin Street and the one in Southern Village.

37 Hike the trails in the Occoneechee Mountain State Natural Area

38 Sip different flavors of honey wine at Starrlight Mead

39 Walk or bike along the banks of the Eno River on the Riverwalk

40 Look sharp in a Carolina blue tie from Julian’s

41 Slurp a milkshake at Sutton’s Drug Store

42 Take a step back in Chapel Hill town history at the Horace Williams House, home to Preservation Chapel Hill

43 Dig into a North Carolina-inspired plate of poutine or a sky-high sandwich at Breakaway Cafe

44 Enjoy a cone at Whit’s Frozen Custard and head to Gold Park with a blanket

45 Bike the 298-mile system of trails in Chatham or take it easy on the Elizabeth “Libba” Cotten Bikeway in Carrboro

46 Belly up to the Lantern bar – or sit outside – for creative dishes from Andrea Reusing, who previously won the James Beard Award for Best Chef Southeast for her blend of Asian flavor with North Carolina ingredients

47 Learn and explore with your kids at Kidzu Children’s Museum

48 Explore the great presents at This & That Gift Gallery or Liquidambar Gallery and Gifts

49 Walk the sidewalks and gallery hop during Last Fridays & The Art Walk in Hillsborough or 2nd Friday ArtWalk in Carrboro and Chapel Hill

50 Have a picnic lunch on a blanket in the Coker Arboretum

51 Explore a classic neighborhood like the Franklin-Rosemary Historic District or Gimghoul Historic District and admire the distinct architecture and beautiful homes

52 Sip award-winning chambourcin at FireClay Cellars, the only commercial vineyard in Chatham County

53 Root for your local high school team at Cedar Ridge High School, Orange High School, Chapel Hill High School, East Chapel Hill High School, Carrboro High School, or, in Chatham County, Northwood High School, Jordan-Matthews High School, Chatham Central High School or Seaforth High School

54 Get a book signed by an author at Purple Crow Books, Flyleaf Books, McIntyre’s Books, Epilogue Books Chocolate Brews or Circle City Books

kids being taught on a field trip
Volunteer Allen Wilson compares two county maps – one with and another without Jordan Lake – during a Chatham County Schools field trip to the historic county courthouse in downtown Pittsboro.

55 Kiss your sweetheart below the Davie Poplar tree on UNC’s campus

56 Join a guided tour at the Historic Chatham County Courthouse and Chatham Historical Museum

57 Dance through an evening of music outside at Fridays on the Front Porch at The Carolina Inn (April-October)

58 Pile a cone high with Carolina Crunch from Maple View Farm

59 Enjoy a relaxing turn down Poet’s Walk at Ayr Mount in Hillsborough

60 Feel like family as you’re greeted by Vincenzo Marrone and Angelo Marrone at Italian Pizzeria III

61 Try some classic calabash-style popcorn shrimp and fish at Dry Dock Seafood

62 Sip a cocktail outside on the porch of the restored The Colonial Inn

63 Catch an afternoon show at Morehead Planetarium & Science Center or go stargazing at Jordan Lake in the evening

64 Pick your medium and let your creative self flow while enjoying a beverage at Wine & Design Chapel Hill

65 Enjoy the beautiful weather – and a pint – at Franklin Motors

people at a pub
Marie Strandwitz, Rosaland Gatewood, Jeff Elliott, Robert Schwarz and Erik Strandwitz enjoy the outdoor space at Franklin Motors on West Franklin Street in Chapel Hill.

66 Pose in front of the iconic “Chapel Hill” mural by artist Michael Brown

67 Learn about the historic Alexander Dickson House, which also serves as the Hillsborough Visitors Center

68 Visit The Cheese Shop in Carrboro – a one-stop shop for all your cheese desires

69 Check out all the funky sculptures and international goods at French Connections and pop by Fragments for unique home decor

70 Shop for trendy pieces at Uniquities, Monkee’s, Whilden or Dovecote

71 Learn about Eastern Carolina-style barbecue at Allen & Son Bar-B-Que or Hillsborough BBQ Company

72 Gobble down late-night cheese fries or loaded sweet potato tots at Linda’s Bar & Grill

73 Enjoy one of the rotating exhibits featuring local and regional artists at the NC Arts Incubator in Siler City

74 Catch a show performed by the Bouncing Bulldogs, a youth jump rope team of international acclaim

75 Learn pottery or drawing in a class at the new, state-of-the-art location of The ArtCenter

76 Try the fried chicken at Bestfood Cafeteria

77 Explore the hottest food and drink spots with a guided Taste Carolina tour

78 Visit the Old Chapel Hill Cemetery on UNC’s campus

79 Head to Silverspot Cinema or The Lumina Theater on Terrific Tuesdays when tickets are a bargain

80 Choose a unique piece for your home from Whitehall Antiques

81 Wait in line on a weekend morning at Sunrise Biscuit Kitchen or have a late-night chicken biscuit at Time-Out

82 Order a hot dog during the UNC baseball season opener at Boshamer Stadium under Carolina blue skies

83 Peruse the art at the Eno Arts Mill or take a mosaic-making class

84 Sip a smoothie or dig into an acai bowl at The Purple Bowl

85 Stroll through the Northside neighborhood as you listen to an audio tour full of stories and history, told by longtime residents and community members

86 Savor vegetarian-friendly dishes at Vimala’s Curryblossom Cafe and Spotted Dog

mom and kids with paddleboard
Heather Cassese has instilled a love of paddleboarding in her two kids, Elizabella and Joden.

87 Check out Mosaic at Chatham Park, a new mixed-used venue with retail stores, restaurants, a coworking space and concert venue

88 Don’t miss the Southern fixins at Mama Dip’s Kitchen

89 Stop by SallyMack Life Furnishings for stylish home goods, jewelry and gifts

90 Celebrate a special occasion with dinner at The Sycamore at Chatham Mills and a nightcap at The Beagle

91 Go see and learn about the wild cats at Carolina Tiger Rescue

92 Paddle in a kayak or canoe out on the waters of the Haw River or rent a boat to cruise or water-ski on Jordan Lake

93 Start the day off right with a big breakfast at Breadman’s or Virlie’s Grill

set of pints at havoc brewing
Havoc Brewing Company’s central downtown Pittsboro location – with its ample seating and regular events that include live music, food trucks and trivia nights – makes it a pleasant place to unwind with friends and family.

94 Choose your favorite cuisine ranging from Japanese and Indian to French and Italian and prepare a four-course meal with guidance from C’est si Bon! Cooking School chefs

95 Tour the Civil War-era Burwell School Historic Site, and learn about the bravery of Elizabeth Hobbs Keckley, who escaped life as an enslaved person to become a close confidant of first lady Mary Todd Lincoln

96 Volunteer at the SECU Family House by preparing and serving meals or dropping off supplies to keep the pantry stocked

97 Sample treats like flan, bolillos, tres leches cake and conchas at Carolina Cravings

98 Have a pint at some of the newest breweries in town – Carrboro’s Haw River Tap & Table or Pittsboro’s Havoc Brewing Company

99 Sip a cocktail at The Crunkleton

100 Spend an afternoon shopping and sampling at The Plant

101 Stroll by Chatham MillsPollinator Paradise Garden and its more than 225 species of perennials, trees, shrubs and grasses – 85% of which are native to North Carolina

Annual Must-Dos


Hunt for eggs and meet the Easter Bunny during the Community Egg Hunt at Southern Community Park

Throw it back with old-school field games, arts and crafts, and more on the lawn in front of St. Joseph C.M.E. Church during the Northside Festival

Run through town during the Tar Heel 10 Miler in April

Check out the local farm scene on the annual Piedmont Farm Tour in April

Take advantage of free cone day at Ben & Jerry’s in April

Bike, climb, dance and perform activities in the streets during Carrboro Open Streets in April

Join a group of Clean Jordan Lake volunteers to remove trash from the shores at the annual spring cleanup

Pet a Clyde Critter – the handiwork of Bynum-based folk artist Clyde Jones – at the Chatham Arts Council’s ClydeFEST in April

Head to Carrboro Day the first Sunday in May

Taste produce during Strawberry Jamboree at Carrboro Farmers Market in May

Enjoy free outdoor performances during the Freight Train Blues Concert Series in May and June at Carrboro Town Commons

Shake your tailfeather at the Spring Chicken Festival, Siler City’s unique street fair


Watch a summer movie under the stars at the Forest Theatre

Commemorate Pride Month in June during Small Town Pride presented by the towns of Carrboro and Chapel Hill

Stroll through downtown Pittsboro’s street fair Summer Fest in early July

Celebrate the Fourth of July at a parade in Carrboro

Watch talented high schoolers taking part in the PlayMakers Repertory Company’s Summer Youth Conservatory on stage during performances of a musical

Get to Southern Village early for a good spot at the Fourth of July fireworks

Take a dip in the Hargraves Community Center pool

Savor tomatoes, the star food of the annual ACME Tomato Festival, and enjoy peak tomato season during Tomato Day at the Carrboro Farmers Market, both in July

See Paperhand Puppet Intervention perform an outdoor show at the Forest Theatre

Watch an outdoor movie on the Southern Village Green

Enjoy music, food and dancing at the annual Latin American Festival in Carrboro in late August


Appreciate live music and traditional folk dancers during the annual Hispanic Heritage Fiesta in September put on by El Vínculo Hispano (The Hispanic Liaison)

Rock out to dozens of bands during the Carrboro Music Festival in September

Listen to music and sip beer and wine during the Bluegrass Festival at historic Moorefields in September

Step back in time at Silk Hope’s annual Old-Fashioned Farmers Day in September

Experience local bands and a barbecue cook-off contest at Hog Day in September

Celebrate mead during Starrlight Mead’s annual Mead Fest in September

Check out the Chatham County Agriculture Fair in September, featuring live performances, rides, children’s activities, food and more

Warm up your taste buds for the outdoor food festival, PepperFest, in Pittsboro

Camp, explore and groove at music festivals at Shakori Hills Community Arts Center, like the Hoppin’ John Fiddlers’ Convention in September and the Shakori Hills GrassRoots Festival of Music & Dance in October

Browse artists’ booths in downtown Chapel Hill during Festifall on three Saturdays in October

Attend readings, workshops and panels during the West End Poetry Festival in October

Sip local brews during NC Beer Month in October

Spook your friends with Halloween fun on Franklin Street

Check out the carved pumpkins on display across the Bynum Bridge and around Fearrington Village in October

Catch films at the Carrboro Film Fest in November

Tour artist studios during the Orange County Artists Guild’s Open Studio Tour in November


Stroll the downtowns to check out decorated shop windows

group at parade
The Chinese School at Chapel Hill’s dragon dance team lit up the December day

Grab a seat for the Light Up The Night Holiday Parade in early December in downtown Hillsborough

Put on your antlers for the Reindeer Run 5K in Pittsboro

Tour the studios of more than 50 local artists in the self-guided Chatham Artists Guild’s Studio Tour during the first two weekends in December

Deck the halls with breakfast with Santa, cookie decorating, holiday tea and markets at The Carolina Inn in December

Sing along at the Bynum Front Porch Christmas Show

See Santa Claus come to town with a live-action performance of Miracle on Hillsboro Street in downtown Pittsboro

Nab a spot on the sidewalk for the Chapel Hill-Carrboro Community Holiday Parade in December

Catch public performances by touring bands, artists in residence, UNC faculty and students at the annual Carolina Jazz Festival in February

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