Valentine’s Day is one of the most searched-for holidays each year especially for valentines date ideas and valentines day date night ideas that feel meaningful and memorable. You’re in the perfect place to plan the best evening in the Triad! Whether you’re looking for romantic dinner spots, fun activities, or unique date experiences around Greensboro, Winston‑Salem, and High Point, this guide has you covered. This list focuses on Valentine’s events and indoor restaurants. Check out our full list of Date Night Ideas in the Triad: Romantic, Fun & Unique Things to Do for more idea no matter the time of year!

Local Valentine’s Events in the Triad – 2026 Edition

Want to make the most of your Valentine’s weekend? Check out these exciting local events happening in Greensboro, Winston‑Salem, and High Point!

Featured Valentine’s Events in the Triad (2026)

Greensboro and Surrounding Areas

Friday, February 13 from 7pm – 8:30pm: Valentine Gala. Enjoy a curated, candlelit evening designed for a memorable night out. The Valentine Gala features a seated steak/chicken dinner with full table service, live music, dessert, and a professional photo to remember the night. On-site childcare is available with select package upgrades, making this an effortless and stress-free date night.

Saturday, February 14 at 7:30pm: Music of the Knights. Join the Greensboro Symphony for their beloved annual Valentine’s Concert, featuring Music of the Knights— a spectacular tribute to three of Britain’s most iconic songwriters: Andrew Lloyd Webber, Paul McCartney, and Elton John. Their legendary hits will be brought to life by three Broadway stars in a night of unforgettable music and romance.

Saturday, February 14 from 6pm – 8pm: Paint Your Partner. Grab your bestie or your boo and join Nailed It for a Paint Your Partner event! Guaranteed laughs, lots of fun, and great memories. Price includes all materials for two people, food & a glass of wine. No experience needed.

Saturday, February 14 at 6pm: Valentine’s Dinner at Summerfield Farms. Celebrate love this Valentine’s Day with an unforgettable evening at Summerfield Farms. Indulge in a romantic five-course meal thoughtfully crafted by 1618 On Location to delight your senses, perfectly paired with five exquisite wines to enhance every bite. Set against the enchanting backdrop of The Barn, this intimate dining experience is designed to create cherished memories with the one you love.

Saturday, February 14 at 7:30pm: 2 Guys Named Chris Comedy All Stars Show. This one of a kind comedy night will feature an array of very talented and witty comedians with unique entertainment styles. The show will feature all-star comedians: E.J. Masicampo, Jeremy Alder & Dave Landau.

Saturday, February 14 (times vary): Valentine’s Day at Wine & Design. They are offering an array of different Valentine’s classes for you and your partner whether you have never painted, or love to paint!

Winston‑Salem and Surrounding Areas

Saturday, February 14 at 10am: Valentine’s Brunch Cooking Class. Join local chef, Mary Haglund, as she returns to the SoHo Kitchen to whip up the ultimate Valentine’s brunch…. incuding special Valentines mimosas!

Saturday, February 14 at 2pm: Chocolate & Wine Pairing – Love is in the air this Valentine’s Day! Head to Shelton Vineyards for a romantic afternoon. It features a curated tasting of six wines paired with a variety of chocolate bites, courtesy of the Harvest Grill.

Saturday, February 14 (times vary): Valentine’s Day at Wine & Design. They are offering two different Valentine’s classes for you and your partner whether you have never painted, or love to paint!

Saturday, February 14 at 6pm: Soap & Candle Making Workshop. Sip champagne or herbal tea, enjoy good vibes, cozy music and raffle prizes while crafting your own custom soap & candles on Valentines Day!

Sunday, February 15 from 12:30pm – 2:30pm: Valentine’s Amore Brunch. Fall in love with Italian flavors at Raffaldini Vineyards Valentine’s brunch cooking class! Join Marla, The Chef in Red for a delightful experience where you’ll learn to prepare delicious Italian-inspired brunch dishes, sip on thoughtfully paired wines, and savor a meal made with love. Perfect for couples, friends, or anyone looking to celebrate Valentine’s Day the Italian way.

High Point/Lexington

Saturday, February 14 at 10am & 1pm – A Valentine’s Day Museum Experience: Love & Legacy. Your ticket includes brunch and participation in a guided tour of the Thankful Heritage Museum’s “To Form a More Perfect Union” exhibit, currently on display at the High Point Museum (HPM). The tour will be followed by Valentine’s Day–themed activities in the HPM gallery.

Saturday, February 14 from 5:30pm – 10pm: Valentine’s Dinner & Dueling Pianos. Enjoy a night of music favorites ranging from Dolly Parton to Bruno Mars! This highly interactive event allows you to choose the songs the pianists play. The night will consist of a gourmet three-course dinner, fine wines, and live musical entertainment with comedic thrills.

Sunday, February 15 at 11am & 2pm: Valentine’s Sweetheart Tasting. Complete your Valentine’s Day with a bubbly tasting of fine sparkling wines paired perfectly with gourmet chocolates from Chocolate Chocolate Chocolate.

Romantic Dinners & Date Night Restaurants in the Triad

When it comes to quality time together, nothing beats a special dinner with great food and ambiance.

Valentine’s Day Restaurants in Greensboro

Green Valley Grill — Classic elevated cuisine paired with an impressive wine list makes this a top romantic restaurant choice in Greensboro.
Print Works Bistro — French‑inspired menus and cozy vibes — a crowd favorite for date nights.
Undercurrent Restaurant — Farm‑to‑table sophistication perfect for an intimate night out.
Cooper’s Hawk Winery & Restaurant — Dine and sip wine with your sweetheart in a stylish setting.
White and Wood
Pangea

Restaurant options in High Point

Earl’s Landing — Upscale dining and handcrafted cocktails make this High Point spot ideal for Valentine’s.
Magnolia Blue — Southern comfort with a creative twist and great beverage pairings.

Recommended Restaurants in Winston-Salem

Romantic & Upscale Options

Spring House Restaurant, Kitchen & Bar – A charming, upscale spot known for seasonal New American cuisine and a romantic historic atmosphere — perfect for a special Valentine’s dinner.
Bernardin’s Restaurant @ Zevely House – Intimate fine dining nestled in one of Winston‑Salem’s oldest homes, ideal for date night celebrations.
Sage & Salt – Creative New American cuisine with craft cocktails and an elegant vibe in the heart of downtown.
The Downtown Grille – Sophisticated steakhouses and seafood with an upscale vibe — perfect for anniversaries or a fancy night out.
Ryan’s Restaurant: A Winston-Salem classic with white tablecloths, prime steaks, and an old-school romantic vibe that’s perfect for a dressed-up Valentine’s dinner.
1703 Restaurant & Bar: Cozy and intimate in the historic West End, 1703 serves seasonal Southern-inspired dishes and cocktails that make for an effortlessly romantic date night.

Casual but Special (& Great for Conversations)

River Birch Lodge – Cozy lodge‑style restaurant with comfort classics — perfect for a relaxed date with rustic charm.
Di Lisio’s – Authentic Italian dishes and a welcoming atmosphere make this a great choice for a romantic yet relaxed date.
Mozelle’s Fresh Southern Bistro – Southern classics with a contemporary flair in a cozy bistro setting — perfect for a quieter conversation date.
Jeffrey Adams on Fourth – Popular local restaurant loved for its eclectic menu and vibrant yet casual environment — great for a fun dinner date.
Betty On Burke – Stylish small‑plates and cocktails ideal for a date that’s more social and playful.
Rooster’s Wood-fired Kitchen Winston Salem – Laid‑back, hearty wood‑fired cooking with a warm vibe — great for an informal but delicious Valentine’s meal.

For more local dining and date inspiration, browse our popular post: Date Night Ideas Across the Triad

Memorable Date Experiences Beyond Dinner

While a romantic dinner sets the mood, adding a fun or meaningful activity can make the night unforgettable.

Enjoy a Show

Tanger Performing Art Center – 2026 Show Schedule
Carolina Theatre — Catch a show, film, or live performance to add an artistic touch to your evening.

Fun & Unique Dates

Bourbon Bowl — Bowling with a twist — cozy seating, drinks, and good laughs.
ParTee Shack (Greensboro) — Mini golf, go‑karts, and arcade vibes for playful couples.
Boxcar Bar + Arcade — Classic arcade games, pinball, skeeball, and drinks — great for a casual date.
Live Music or Adult Couples Events — Keep an eye on local Eventbrite listings for February date night events like live music, couples dances, or themed parties.

Creative & Interactive Activities in Winston‑Salem

Art, Museums & DIY — From painting classes to gallery strolls or bike rides (like Salem Creek Greenway), Winston‑Salem’s creative scene is perfect for a memorable date.

At‑Home & Cozy Date Night Alternatives

Prefer to stay in? Cozy can still be romantic and fun — and we’ve got the perfect ideas for you!

Create a themed at-home party: At-Home Valentine’s Day Party Ideas for All Ages
Share the love with gifts: Valentine’s Day Gift Guide

Curl up with a good book: Valentine’s Day Books

Tips for Planning the Perfect Valentine’s Date Night

Plan Ahead – February dining reservations fill quickly — especially for Valentine’s Day weekend.
Mix Experiences – Pair dinner with a show, walk, or activity to make the night feel unforgettable.
Think Local – Supporting Triad businesses like restaurants, breweries, and venues makes your evening extra special.

Whether you’re going out or staying in, Valentine’s Day in the Triad offers something for everyone. Use these cute, romantic, and fun date ideas to spark connection and create unforgettable memories — right in your own backyard.

Other Blogs You Might Like:

How to Celebrate Valentine’s Day at Home

Unique valentines class gifts

At-Home Valentine’s Day Party Ideas for All Ages

Asheville Romantic Getaway: Couples’ Adventures, Date Ideas & Hidden Gems

Healthy, Festive Valentine’s Day Food Ideas for Kids