Curtin Team Picks: Date Night in (& around) Roswell

Just up the hill from the Roswell Mill and Vickery Creek, Proper Hop is the perfect spot to wind down after the trails with craft beer, rotating weekend food pop-ups, and draft whiskey cocktails. Keep it casual upstairs/outside on the patio or head downstairs to the tucked-away (21+) lounge for a more intimate night out.

Fermented brings a more interactive spin to wine night with rotating tastings, themed wine flights, workshops, and social events ranging from wine education nights to private gatherings and live experiences. Located in the heart of Downtown Alpharetta (with a second location in Canton), it’s an easy pick for date night, girls night out, or anyone looking for something beyond just dinner and drinks.

Matilda’s isn’t your typical concert venue — it’s an intimate outdoor music spot tucked into the trees in Milton/Alpharetta where guests bring lawn chairs, coolers, and settle in for live music under the pines. With food trucks, local artists, and a laid-back backyard feel, it’s one of the most unique date night spots north of Atlanta.

The Velvet Note is less of a typical music venue and more of an intimate listening-room experience, designed around acoustics and live performance. Open Wednesdays, Thursdays, Fridays, Saturdays, and Sundays, guests can purchase tickets for live jazz performances while enjoying dinner, cocktails, and a cozy atmosphere that feels elevated and completely different from a larger concert venue.

Skip the usual dinner reservation and head to the river instead. Chattahoochee Nature Center hosts adults-only Date Night canoe trips on select Fridays throughout spring and summer — bring your own picnic and drinks, then enjoy a guided sunset paddle on the Chattahoochee.

Looking for a more interactive date night? Taste Buds Kitchen offers hands-on cooking classes in Alpharetta ranging from fresh pasta and sushi making to tapas, Thai dishes, pizza nights, and more. Classes are beginner-friendly, BYOB (wine and beer welcome), and designed for couples, friends, and group nights out — all in a relaxed, social kitchen setting.

If you’re looking for a spot that feels a little more special than the usual dinner reservation, Truth Be Told delivers ✨ Known for its craft cocktails, patio seating, tasting menu options, and upscale-but-welcoming atmosphere in Downtown Roswell.

The Gaslight brings an old-school supper club feel to Downtown Roswell with live music, handcrafted cocktails, and a lively late-night atmosphere. Their Tuesday–Thursday happy hour features half-price raw and baked oysters from 5–6:30 PM, making it an easy night-date stop before heading to Canton Street.

Deep Roots is one of Downtown Roswell’s favorite spots for a relaxed night out, with a cozy outdoor patio, self-pour wine tastings, and a full calendar of events ranging from Wine-O Bingo and Mahjong nights to pairing dinners and themed tastings. It’s an easy place to meet friends, ease into date night, or linger over a glass before dinner on Canton Street

Catch nationally touring comedians without commuting all the way into Atlanta. Located in Alpharetta, Helium Comedy Club brings big-name acts, themed shows, and weeknight entertainment to an intimate venue with full food and drink service — perfect for an easy date night or group outing.

Pack a lawn chair and head to the Alpharetta Town Green for free live music all summer long. The Friday night concert series runs May through September and makes the perfect low-key date night — especially with Downtown Alpharetta’s restaurants, patios, and happy hour spots just steps away before the show.

Located in the heart of Milton/Crabapple, Six Bridges Brewing is one of the area’s go-to community hangouts. With weekly trivia, music bingo, live music weekends, a rooftop patio, dog-friendly seating, and in-house BBQ from Spiced Right, there’s almost always something happening beyond just grabbing a beer.

Looking for a slower-paced date night? Painted Horse blends vineyard views, live music, wine tastings, and outdoor seating into one of the most unique spots in Milton. The winery hosts live music Wednesday through Sunday on “The Green,” plus rotating events like wine dinners, cellar tastings, Mahjong nights, and seasonal workshops — all just outside Alpharetta. Arrive early for a wine flight, stay for the sunset and live music, and settle in for a relaxed night under the string lights. 

Looking for something a little different for date night? Roswell Ghost Tours offers guided walking tours through Historic Downtown Roswell every Friday and Saturday evening, sharing local legends, eerie history, and haunted tales tied to some of the area’s oldest buildings and streets.

Fetch Park is the perfect spot to enjoy a drink (or two) without having to leave the pup at home. This fully off-leash dog park doubles as a social hangout with a full-service bar, live music, trivia nights, music bingo, and outdoor TVs — making it just as fun for humans as it is for dogs.

Ground & Pound Coffee is one of the few spots around Alpharetta where you can still grab a coffee after dinner. Open late Wednesday through Saturday, the space shifts from daytime coffee shop to neighborhood hangout with live music, trivia nights, comedy shows, Sip & Paint events, cocktails, wine, and late-night lattes. A great alternative to the typical bar scene.

From country and rock to indie, pop, and orchestra nights, Ameris Bank Amphitheatre is one of North Atlanta’s go-to outdoor music venues. Grab dinner in Downtown Alpharetta beforehand, then head over for a concert under the stars with lawn seating, food and drink options, and major touring artists all season long. You can reserve lawn chairs, upgrade to premium lounge seating, or tailgate before the show to make a full night of it.

Wrap up date night with a walk through Avalon and a stop at Jeni’s for dessert. Grab a scoop to enjoy while wandering the plaza, or take a pint home to keep the night going a little longer.

Known for their signature flower-shaped gelato cones, Amorino is a fun post-dinner stop at Southern Post in Roswell. Grab gelato, sorbet, or macarons and wander the courtyard or patio spaces nearby for an easy, low-key dessert date.