Our Favorite Date Night Spots by Town
Whether it’s Valentine’s Day, an anniversary, or a spontaneous Friday night out, Fairfield County offers some of the most romantic restaurants in Connecticut. From waterfront dining to cozy candlelit taverns and refined wine bars, there’s no shortage of places to celebrate love.
At Fowler Sakey Team – Coldwell Banker Realty, we believe loving where you live also means loving where you dine. One of the things that makes Fairfield County so special is the vibrant dining scene woven into every town center.
Here’s our curated guide to the best romantic restaurants in Fairfield County — organized by town.
🌊 Southport, CT
Artisan Restaurant, Tavern & Garden
Elevated American cuisine in a refined yet relaxed setting — perfect for a cozy, upscale evening in Southport Village.
Paci Restaurant
A warm, intimate Italian restaurant tucked into Southport’s charming downtown. Think handmade pasta, candlelight, and a relaxed coastal vibe.
🌅 Stratford, CT
Riverview Bistro
Water views + contemporary American fare. A hidden gem ideal for sunset dinners and special occasions.
🍷 Stamford, CT
Columbus Park Trattoria
Classic Italian dishes in an intimate downtown Stamford setting.
Divina
Modern Italian cuisine with a sophisticated atmosphere — perfect for a polished date night.
Prime: An American Kitchen & Bar
Upscale waterfront dining in Harbor Point — ideal for celebrations and milestone moments.
🌿 Westport, CT
Westport continues to be one of the most desirable dining destinations in Fairfield County.
The Cottage
A charming New American restaurant with serious date-night appeal.
Bistro Du Soleil
A classic French bistro along the Saugatuck River — romantic and timeless.
Le Penguin
Elegant French cuisine in an intimate dining room.
The Boathouse
Waterfront dining with sunset views that never disappoint.
Gabriele’s of Westport
Refined steakhouse dining with an elevated atmosphere.
🏫 Wilton & Georgetown, CT
Baldanza at the Schoolhouse
Intimate Italian dining in a beautifully restored historic schoolhouse.
Milestone Restaurant
Rustic charm meets creative American cuisine — perfect for a relaxed yet memorable evening.
🌆 Bridgeport, CT
29 Markle Ct
Stylish and energetic — ideal for couples who enjoy a lively date night atmosphere.
🌊 Darien, CT
Water’s Edge at Giovanni’s
Italian cuisine paired with waterfront views — romance guaranteed.
⚓ Greenwich, CT
L’Escale
French coastal elegance overlooking Greenwich Harbor.
Tony’s at the J House
Modern Mediterranean flavors in a chic boutique setting.
🏡 Fairfield, CT
Esh Modern Mediterranean
Bold flavors in a warm, intimate setting.
Barcelona Wine Bar – Fairfield
Tapas, wine, and cozy corners made for sharing.
Il Pellicano
Classic Italian cuisine with a welcoming, romantic feel.
The Sinclair
Refined dining right in the heart of Fairfield.
🌄 New Canaan, CT
Roger Sherman Inn
Historic New England charm meets fine dining.
Cava Wine Bar & Restaurant
An intimate wine bar perfect for lingering evenings.
🌊 Norwalk, CT
Tavern at GrayBarns
Rustic elegance with seasonal American fare.
Match – South Norwalk
Modern American cuisine with vibrant energy.
Washington Prime – South Norwalk
Sophisticated steakhouse with warm ambiance.
🌳 Ridgefield, CT
Bailey’s Backyard
Farm-to-table charm in downtown Ridgefield.
Luc’s Café & Restaurant
Classic French cuisine in a cozy, romantic setting.
Discover Local with Fowler Sakey Team
We love sharing what makes Fairfield County special — from romantic restaurants to hidden neighborhood gems.
Thinking about buying or selling in Fairfield County?
📍 Fowler Sakey Team – Coldwell Banker Realty
📞 475-888-9713
Because home is more than a place — it’s the life you build around it.