Looking for the ultimate bucket list for Orange County and Chatham County? Look no further than our curated guide! From hiking trails to local eats, our list has everything you need to experience the best of these two beautiful North Carolina counties. Our list will help you discover hidden gems and must-see attractions that you won’t want to miss. So grab your friends and family, and start checking off these must-do activities on your Orange County and Chatham County bucket list today!
Photography by John Michael Simpson
1 Rush Franklin Street after a UNC victory over Duke
2 Go see and learn about the wild cats at Carolina Tiger Rescue
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 Visit Chapel Hill’s most perfect sunset spot – Merritt’s Pasture
6 Groove to a favorite band at Cat’s Cradle or catch an up-and-coming hip-hop artist at Local 506
7 See the Belted Galloway cows and stroll the walkable Fearrington Village
8 Finish a blue cup at He’s Not Here
9 Release some steam by ax-throwing at Chatham Axes
10 Don’t miss the Southern fixins at Mama Dip’s Kitchen
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 Tar Heel hoops history at the Carolina Basketball Museum
14 Better yet, cheer on UNC during the Dean E. Smith Center or watch it at Four Corners
15 Enjoy one of the rotating exhibits featuring local and regional artists at the NC Arts Incubator in Siler City
16 Try a Bell Tower Blueberry Wheat beer at Top of the Hill
17 Drink from the Old Well
18 Join a guided tour at the Historic Chatham County Courthouse and Chatham Historical Museum
19 Play a round of golf at the newly renovated UNC Finley Golf Course
20 Nibble on a nutty fruitcake at Southern Supreme Fruitcake & More
21 Order a single, double, or, if you dare, a triple BLT at Merritt’s Grill
22Get 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 Enjoy the latest exhibition at the Ackland Art Museum or stroll through the artist-owned FRANK Gallery in University Place
24 Take a nature walk at the North Carolina Botanical Garden
25 Greet the UNC football team and cheerleaders as they make their way to Kenan Stadium durning the pregame Victory Walk
26 Memorize the lyrics of James Taylor’s “Carolina in My Mind“
27 Catch a show performed by the Bouncing Bulldogs, a youth jump rope team of international acclaim
28 Pile a cone high with Carolina Crunch from Maple View Farm
29 Sip different flavors of honey wine at Starrlight Mead
30 See a Carolina Performing Arts show at CURRENT ArtSpace + Studio or Memorial Hall
31 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
32 Relax on the lawn of Weaver Street Market in Carrboro
33 Enjoy a pickup game of mahjong or pingpong or take a Zumba class at the Seymour Center
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 Use your Italian dinnerware purchased at the VIETRI outlet store in Hillsborough
36 Buy a cut of meat from Cliff’s Meat Market
37 Hike the trails in the Occoneechee Mountain State Natural Area
38 Go on a burger tour with stops at Johnson’s Drive-In in Siler City and Buns and Al’s Burger Shack in Chapel Hill
39 Walk or bike along the banks of the Eno River on the Riverwalk
40 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 flavors with North Carolina ingredients
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 Look sharp in a Carolina blue tie from Julian’s
45 Enjoy a cone at Whit’s Frozen Custard and head to Gold Park with a blanket
46 Bike the 298-mile system of trails in Chatham or take it easy on the Elizabeth “Libba” Cotten Bikeway in Carrboro
47 Sip award-winning chambourcin at FireClay Cellars, the only commercial vineyard in Chatham County
48 Pick up a six-pack at Beer Study or The Casual Pint
49 Explore the great presents at This & That Gift Gallery or Liquidambar Gallery and Gifts
50 Walk the sidewalks and gallery hop durning Last Fridays & The Art Walk in Hillsborough or 2nd Friday ArtWalk in Carrboro and Chapel Hill
51 Have a picnic lunch on a blanket in the Coker Arboretum
52 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
53 Explore a historic residential neighborhood like the Franklin-Rosemary Historic District or Gimghoul and admire the distinct architecture and beautiful homes
54 Feel like family as you’re greeted by Vincenzo Marrone and Angelo Marrone at Italian Pizzeria III
55 Kiss your sweetheart below the Davie Poplar tree on UNC’s campus
56 Dance through an evening of music outside at Fridays on the Front Porch at The Carolina Inn (April-October)
57 Learn and explore with your kids at Kidzu Children’s Museum
58 Dig into Sunday brunch by Beau Catering at The Colonial Inn
59 Enjoy a relaxing turn down Poet’s Walk at Ayr Mount in Hillsborough
60 Shop for trendy pieces at Uniquities, Monkee’s, Whilden or Dovecote
61 Get a book signed by an author at Purple Crow Books, Flyleaf Books, McIntyre’s Books, Epilogue Books Chocolate Brews or Circle City Books & Music
62 Try some classic Calabash-style popcorn shrimp and fish at Dry Dock Seafood
63 Learn about the historic Alexander Dickson House, which also serves as the Hillsborough Visitors Center
64 Catch an afternoon show at Morehead Planetarium & Science Center or go stargazing at Jordan Lake in the evening
65 Peruse the art at the Eno Arts Mill or take a mosaic-making class
66 Pose in front of a Michael Brown mural
67 Get your work clothes and see where Charlie Daniels Played his first paying gig at JR Moore & Son in Gulf
68 Start the day off right with a big breakfast at Breadman’s or Virlie’s Grill
69 Check out all the funky sculptures and international goods at French Connections and pop by Fragments for unique home decor
70 Visit the Old Chapel Hill Cemetery on UNC’s campus
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 Dine al fresco in the outdoor garden at Kipos
74 Satisfy your sweet toth with a slice of cake at Nantucket Grill or a creative confection at Glasshalfull
75 Learn pottery or drawing in a class at The ArtCenter
76 Try the friend chicken at Bestfood Cafeteria
77 Explore the hottest food and drink spots with a guided Taste Carolina tour
78 Stroll on one of our many beautiful greenways, like the Tanyard Branch Trail, where metalwork art is on display by local artist Leo Gaev
79 Sip a cocktail at The Crunkleton
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 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
84 Tour the Civil War-era Burwell School Historic Site, and learn about the bravery of Elizabeth Hobbs Keckley, who escaped life as a slave to become a close confidant of first lady Mary Todd Lincoln
85 Sip and paint at Carrboro’s Steel String Brewery, Haw River Ales/Vecino Brewing Company or Pittsboro’s Carolina Brewery, BMC Brewing and Red Moose Brewing Company
86 Savor vegetarian-friendly dishes at Vimala’s Curryblossom Cafe, Sage Vegetarian Cafe and Spotted Dog
87 Check out Mosaic at Chatham Park, a new mixed-used venue with retail stores, restaurants, a coworking space and concert venue
88 Choose among different tasty salsas at Carrburritos
89 Stop by Steel Roots Home Decor for stylish yet functional home goods
90 Celebrate a special occasion with dinner at The Sycamore at Chatham Mills and a nightcap at The Beagle
91 Order a coffee and treat at The Chatham Rabbit in Siler City or at Aromatic Roasters in Pittsboro
