Even the most jaded soul might find themselves charmed by the youthful and vibrant chaos that is Glenwood South! This district, pulsing with a big-city heartbeat, offers a variety of entertainment. Thirsty explorers will discover a bounty of bars and restaurants, each vying for your attention with their own alluring quirks. When it comes to planning an exhilarating Raleigh date night, Glenwood South has it all.

For the perfect Glenwood South date night, you should definitely start with a fun activity, get drinks, have a tasty meal, and save room for dessert.
This post contains affiliate links and I may earn a small commission when you make a purchase using the links at no additional cost to you.
How to plan a Raleigh date night on Glenwood South
Step 1: A Fun Activity
These fun activities are all perfect for an exhilarating Glenwood South date night.
Test your spy skills at NERD Escape Room Raleigh – 117 Glenwood Ave – If you like mind-bending puzzles and original storylines, NERD Escape Room has you covered! Their in-house designed adventures offer a unique challenge for escape room enthusiasts of all experience levels.
See some live music at Tin Roof Raleigh – 300 Glenwood Ave – This restaurant and bar has daily live music from various genres.
Watch some sports at Carolina Ale House –500 Glenwood Ave Suite 300 – This chain offers a relaxed spot for catching the game and enjoying a meal. Choose from hearty pub classics, an extensive beer list, and a dedicated kids’ menu – in case your sitter cancelled at the last minute.
Step 2: Grab Some Drinks

Glenwood South has endless possibilities for drinks, whether you want a handcrafted cocktail, a nice glass of wine, or a simple beer in a dive bar. Who says romance is dead?
Dram and Draught – 1 Glenwood Ave Suite 101 – Dram and Draught is an old-school whiskey bar known for hand-crafted cocktails. There is an extensive list of cocktails featuring seasonal creations, house favorites, and twists on classic cocktails, as well as wine and zero-alcohol creations. For those wanting to sample from Dram & Draught’s extensive whiskey list there is a flight with a choice of three one-ounce pours.
Killjoy – 116 N West St – Killjoy creates unique cocktails for each customer depending on their preferences. They also have a huge selection of recommended cocktails and mocktails on their menu.
Raleigh Beer Garden – 614 Glenwood Ave – Check out this beer paradise with over 350 on tap, plus delicious modern comfort food! Enjoy it all in a stylish bi-level space with a huge patio.
Johnson Street Yacht Club – 710 W Johnson St – This is a dive bar with rooftop patio and a “hella fast” slide. What better way to add a little whimsy to your date?
Step 3: Have Dinner
While Glenwood South offers a huge variety of dining options, here are a few that create the perfect ambiance for a romantic date night in Raleigh.
Cortez – 413 Glenwood Ave – Cortez serves oysters, NC seafood, and magical vegetables, often with a Mexican spin. Don’t sleep on the side of buttered beans.
Vidrio – 500 Glenwood Ave #100 – Dine in a stylish atmosphere featuring dramatic decor. Enjoy exquisite Mediterranean fare and creative cocktails. Reservations recommended.
La Santa – 222 Glenwood Ave #107 – La Santa is a vibrant and relaxed Mexican eatery with unique decor, daily lunch specials, and a killer tequila cocktails. Their patio offers great views for people watching in case your date is dull.
Mojoe’s Burger Joint – 620 Glenwood Ave – This relaxed spot with a spacious outdoor seating area, is perfect for grabbing burgers, wings, and classic pub fare. You’re going to want to share a basket of beer-battered onion rings.
Step 4: Get Dessert
Saving room for something sweet to wrap up your Raleigh date night on Glenwood South? Here’s where to go to satisfy that sweet tooth.
The Cupcake Shoppe Bakery + Coffee – 104 Glenwood Ave – The Cupcake Shoppe is a stylish little bakery creating custom cakes and cupcakes, alongside pastries and espresso drinks.
Where to Park Around Glenwood South
Street parking can be found along Glenwood South and other nearby streets. Be sure to read the signs to determine where and when you’re allowed to park and pay for parking using the Passport Parking app.
If you can’t find street parking, there are also a few parking decks which can be paid for upon exiting.
When ending a scooter trip on Glenwood Avenue between W Johnson Street and Hillsborough Street, users should only end their trip in a scooter parking corral. Here is a map of the scooter parking corrals.
Read more about parking and getting around downtown Raleigh here.
Where to Stay Around Glenwood South
If you’re visiting from out of town or decide to make a staycation of your Glenwood South date night, consider staying at the AC Hotel, a comfortable Mediterranean hotel, The Casso, another comfortable hotel with 24-hour fitness, or the Hampton Inn, which offers everything you’d expect from a Hampton Inn.
Where to Get Coffee and Breakfast in Glenwood South

321 Coffee – Downtown – 615 Hillsborough St – 321 Coffee employs over 50 adults with intellectual and developmental disabilities who roast the coffee, serve customers, and craft delicious lattes. The seating here is mostly on their patio.
Iris Coffee Lab – 725 Tucker St – Iris Coffee Lab is a light and bright industrial style cafe with big windows and so many Fiddle Leaf Figs and large Snake Plants. They have a full espresso menu with tasty seasonal drinks and a selection of sandwiches to fuel your day. There is plenty of seating indoors and a small sidewalk patio area.
Which of these Raleigh spots would you choose for a Glenwood South date night?
Save this post for later on Pinterest:







Please leave a reply as proof you were here