When it comes to planning the perfect Raleigh date night, Five Points is a haven of delights.

Five Points is comprised of a handful of historic suburbs radiating out from the intersection of Glenwood Avenue with Whitaker Mill and Fairview roads. It was originally developed from the late 1910s to 1950s and is home to several old neighborhood haunts that have become Raleigh institutions. But it has also become a popular area for bright-eyed newcomer restaurants and breweries, eager to tantalize your taste buds with culinary novelties.

Five Points Mural on Fairview Road
Five Points Mural on Fairview Road

For the perfect Five Points date night, you should definitely start with a fun activity, get drinks, have a tasty meal, and save room for dessert.

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How to Plan a Raleigh Date Night in Five Points

Step 1: A Fun Activity

The Rialto Theater
Check out a show at The Rialto

These fun activities are all perfect for a delightful Five Points date night.

Work up an appetite at Raleigh Pilates2003 Fairview Rd STE B – Join a group class or book a semi private session to receive hands on instruction and a tailored movement routine, regardless of past pilates experience. You’ll find yourselves contorted into human question marks, forever seeking the answer to “why are we doing this?”

Seek some relaxation at Tao Day Spa2012 Fairview Rd #B – Let skilled hands knead away the knots of worry, molding your once-tense muscles into fluffy marshmallows of contentment. Or consider a transformative mani-pedi leaving your nails gleaming like polished gemstones. Skincare, waxing, and more are also offered at this cozy day spa.

Catch a show at The Rialto1620 Glenwood Ave – Check the events schedule to see anything from live music to comedy to independent films in this revamped 1940s theater.

Step 2: Grab Some Drinks

Five Points Wine
Enjoy a wine tasting at Five Points Wine

Whether you’re in the mood for a classy glass of wine, a chill beach bar, a honky tonk, a chill brewery or bottle shop, or something non-alcoholic, you’ll find plenty of places to grab a drink in Five Points.

Crafty Beer, Wine & Spirits2005 Fairview Rd – This is cozy bottle shop and neighborhood bar. Their focus is North Carolina beers but they also offer a selection of cocktails and wine by the glass.

Five Points Wine2002 Fairview Rd – This is an upscale boutique wine shop. Stop in for a tasting and don’t be surprised if you end up taking a couple bottles home.

Lola’s Beach Bar1803 Glenwood Ave – This place truly has chill beach bar vibes in the middle of Raleigh. Their beer selection is focused on Mexican, Caribbean, and easy drinking American ales and lagers. Their cocktails are what you’d expect to be drinking on the beach and they even sell margarita pitchers!

Neuse River Brewing & Brasserie518 Pershing Rd – This is a casual and inviting brewery focused on Belgian beers and IPAs alongside a varied European-inspired food menu. Sit on the patio and enjoy good company alongside the herb and hops garden.

Nickelpoint Brewing Company506 Pershing Rd – Located just up the road from Neuse River Brewing, Nickelpoint offers a variety of beer styles but I’m particularly fond of their Belgian Golden. They offer beer flights so you can sample a few and they have wine as well. They also have a number of board games and yard games to keep you entertained in the taproom or on the patio.

Tao Boba Tea2003 Fairview Rd E – This bubble tea spot is a great option if you want to get a drink but don’t want alcohol.

Taste, Small Plates & Wine Bar1912 Bernard St – This is a cozy, art-filled wine and cocktail bar also serving Thai and American small plates.

Uncle Jessie’s Honkytonk1622 Glenwood Ave – This place has Nashville vibes with live country music every thursday through sunday starting at 9:30. p.m. so it could be a really fun option for after-dinner drinks.

Step 3: Have Dinner

Creamed Feta at Ajja
Go to Ajja. Get the Creamed Feta. Have a great date.

With plenty of great spots for a bite to eat in Five Points, these are some of the best ones for a date night in Raleigh.

Ajja209 Bickett Blvd – A lively, beautiful, vibrantly decorated restaurant serving Mediterranean and Middle Eastern inspired food and fantastic cocktails. Nothing on the menu will leave you disappointed, but I’m an especially big fan of the Warm Squash Dip, Creamed Feta, Warm Moroccan Hummus, and King Trumpet Mushrooms. Get a reservation and sit on the patio if you can.

Bloomsbury Bistro509-101 W Whitaker Mill Rd – Elevated French influenced food served in a dining room with white tablecloths. The menu changes seasonally based on the availability of fresh local ingredients.

J. Betski’s1916 Bernard St – Bright, industrial restaurant with an elegant yet casual vibe serving up German and Polish food. If the weather is good, sit out on the patio and sample some of their pierogis. I usually get the Sausage Plate but could also be happy making a meal of several of their sides such as the Braised Sauerkraut, Cabbage Wedge, Cheese Spaetzle, and Cucumber Salad.

Lilly’s Pizza1813 Glenwood Ave – Funky casual pizza spot serving pizzas with a hearty, lightly sweet crust. Local favorites include the Big Star (Creamy Pesto, Mozzarella, Gorgonzola, Fontina, Roasted Red Peppers, Parmesan & Pistachios) and The Gus (Porcini Mushroom Oil, Roasted Garlic, Buttoncap Mushrooms, Shiitake Mushrooms, Portobello Mushrooms, Sharp Cheddar, Parmesan & Fontina).

Mandolin2519 Fairview Rd – This is a global fiesta for your taste buds – reimagined Southern classics with unexpected twists. Their daily-changing menu, bursting with market-fresh flavors, guarantees there’s always something new to discover.

Step 4: Get Dessert

Saving room for something sweet to wrap up your Raleigh date night in Five Points? This is the perfect final stop.

Hayes Barton Cafe & Dessertery2000 Fairview Rd – This place has 1940s diner vibes and serves huge, delicious slices of pie and cake.

Where to Park Around Five Points

There is free street parking on many of the streets radiating out from the Five points intersection as well as throughout the neighborhoods. Check the signs as parking may be restricted at certain times of day, particularly along Glenwood Avenue where the parking lane converts to a driving lane during rush hour.

Where to Stay Around Five Points

If you’re visiting from out of town or decide to make a staycation of your Five Points date night, a short term rental right in the neighborhood would be a great option. The Whimsical Raleigh Mill House, the Lovely, Spacious Home, and the True Southern Comfort all look great and have glowing reviews.

Where to Get Coffee and Breakfast in Five Points

The Third Place coffee house
Check out The Third Place for cozy coffee house vibes

If you stayed the night, here are a few places to check out for coffee and or breakfast.

The Third Place1811 Glenwood Ave – This is a very warm and cozy coffee house filled with overstuffed armchairs, art, and antiques. They serve a variety of coffee and espresso drinks, as well as teas, smoothies, pastries, sandwiches, and salads.

Bright Spot Donuts1501 Sunrise Ave suite 180 – Bright Spot is a bright and modern donut shop with a sunny patio. Get it? I highly recommend the Sourwood Honey donuts, but all of the donuts are heavenly. They also offer a limited coffee menu and a few savory items if you’re not feeling sweet.

Idle Hour Coffee Roasters1818 Oberlin Rd #103 – This light and bright coffee shop is filled with plants and sunshine. They have unique espresso drinks but also offer a number of treats from local bakeries such as Tepuy Donuts, Little Blue Macaron, Michaels English Muffins, mini cheesecakes, and sandwiches made with Union Special bread.

Want a bigger brunch? Here are some suggestions.


Which of these Raleigh spots would you choose for a Five Points date night?

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