The Best Happy Hours in Westport

Most widely known for its picturesque landscapes and affluent communities, Westport, Connecticut, also boasts a vibrant restaurant and bar scene. Within that excellent collection of dining establishments are a handful of happy hours, including local favorites and well-regarded spots in international fare. From great settings to friendly atmospheres to drink and food specials, Cindy Raney & Team presents a guide to some of the best happy hours in Westport - all of which offer outdoor dining!

Overlooking the Saugatuck River, BarTaco distinguishes itself by its location and enticing "High Tide" Happy Hour. Available Monday to Friday from 3 PM to 6 PM and a late-night window from 9:30 PM until close from Monday to Thursday, this spot is perfect for those who appreciate a refreshing after-work or after-hours cocktail. The bar features a newly enhanced menu of fresh-squeezed cocktails priced at $8.50, alongside $6.50 wines, sangrias, and $4.50 beers. It's a prime location to relax with friends and colleagues and savor your drinks and small bites, offered exclusively at the bar.

Located in Westport's historic original town hall, Don Memo celebrates Mexican culture with inspiration drawn from the vibrant streets of Mexico City, Oaxaca, and Puebla. Their Feliz Hora—Spanish for Happy Hour—runs from Tuesday to Friday between 4:30 PM and 6:00 PM. Embrace the spirit of Mexico with $6 spirits and soda, $4 selected beers, and $5 selected wines. The venue radiates an organic, vibrant ambiance that will elevate your casual dining and drinking experience. Their patio space is unmatched, creating the perfect setting for an after work drink with friends.

Occupying the historic Sherwood House, which dates to the early 1800s, the Spotted Horse Tavern is a late-afternoon favorite thanks to its daily happy hour from 2:30 PM to 5:30 PM. That means whether it's a post-work cocktail or a weekend gathering of friends, you'll find an accommodating happy hour in the heart of downtown. Also popular are the tavern's daily themes, including ½ price Martini Mondays, discounted tacos and Mexican beers on Taco Tuesdays, Wine and Dine Wednesdays with significant discounts on wine bottles, and $7 Sangria Sundays. Every Spotted Horse happy hour includes daily drink and food specials in the bar area.

For those who appreciate a sophisticated home and garden vibe with their happy hour, Westport's go-to store for luxury-minded green thumbs, Terrain, also features the quaint, greenhouse-inspired Terrain Cafe. With a bar menu designed specifically for post-work afternoon to evening transitions, patrons can partake in $5 draft beers, cocktails like the $8 Pomegranate Mule, and bar menu discounts every Monday through Friday from 4 PM to 6 PM.

Nestled along the Saugatuck River, The Whelk boasts a vibrant seafood bar and restaurant in Saugatuck. Its ever-evolving menu champions sustainable seafood and local produce, ensuring freshness and flavor. Whether you opt for private tables, communal seating, or the inviting bar, The Whelk promises a laid-back vibe perfect for savoring coastal delights. With outdoor seating available, guests can soak in the riverside ambiance.

Positioned in the heart of downtown Westport, Nômade draws culinary inspiration from global destinations like North Africa, Santorini, Asia, Hungary, Spain, France, and the Mediterranean. This eclectic fusion results in a menu bursting with diverse flavors and cultural influences. Set amidst the energetic backdrop of Westport's bustling main street, it’s a great place to pop in for a drink or a bite to eat outdoors. The bar is always a lively spot!

Overlooking the picturesque Saugatuck River and Long Island Sound, La Plage embodies the essence of waterfront dining in Westport. This casual yet refined restaurant and oyster bar showcases coastal cuisine, highlighting locally harvested seafood, shellfish, garden-fresh produce, and sustainable meats. Guests can relish in a relaxed atmosphere while enjoying panoramic views of the waterfront, creating a dining experience that harmonizes with the natural beauty of its surroundings. Enjoy outdoor dining on their large patio, or grab a drink and relax on the lawn. It’s one of the prettiest views in Westport!

Westport's happy hour scene offers something for everyone, from waterfront views at The Black Duck Cafe to the garden-inspired elegance at Terrain Cafe. Each venue provides a unique experience that encapsulates the charm and sophistication of Westport.

You'll uncover a similar theme in Westport's luxury real estate scene, which includes stunning coastal and riverfront homes and secluded multi-acre estates. If you're ready to discover more about luxury Westport homes, contact Cindy Raney & Team today for the best combination of experience and expertise. You'll quickly discover that happy hour in Westport is every hour of the day.