above: (left) Fresh oysters from La Plage. (middle) Enjoy a delicous meal with views of the Saugatuck River and Long Island Sound. (right) Some of La Plage’s craft cocktails. – Photographs; food by Andrea Carson; drinks and porch by Garvin Burke; others by restuarants
1 La Plage at Longshore
There is perhaps no better place to spend a sunny afternoon in the summer than sitting outdoors at La Plage at Longshore—the casual, waterfront restaurant and oyster bar showcasing what the restaurant says is “a coastal cuisine focused on locally harvested seafood and shellfish, garden fresh produce and sustainable meats,” served in a relaxed atmosphere with views of the Saugatuck River and Long Island Sound. The views and atmosphere this restaurant offer are second to none. Locals Night Sunday, offered Sunday afternoons from 4 to 8 p.m., features an extensive food menu for adults and kids alike, plus an extensive wine (by the bottle and by the glass), beer, craft cocktail and mocktail list offering something for everyone. My favorite is The Lilac, a refreshing, nonalcoholic blend of summer flavors like hibiscus and pineapple. Delish.
2 Allium Eatery
This cozy, tiny (and we mean literally—there’s seating for only 14 in the restaurant, plus six at the bar) gem expands its seating capacity in the warmer months (May through October, weather permitting) with an outdoor area that accommodates an additional 20 guests. Located on Railroad Place, directly across from the Westport Train Station, Allium is the perfect spot to enjoy a high-end pit stop on your way home from the city. Chef Michelle Greenfield was recently a 2025 James Beard Awards semifinalist for best chef in the Northeast. Drink offerings here are extensive and rotate seasonally—ranging from white, red, and sparkling and rosé by the glass; nonalcoholic, “zero-proof” mocktails and beers; some get-your-engines running cocktails; and day-ending nightcaps. Allium also focuses on carrying spirits and wines from smaller, family-owned businesses, as opposed to bigger-name brands. If you’re in the mood for a nosh, Allium delivers, with chef Greenfield and team crafting ever-changing menus and evolving dishes specially crafted to incorporate and also celebrate the freshest ingredients each season has
to offer.
3 The Bridge at Saugatuck
Another Westport newcomer, The Bridge at Saugatuck, located along the banks of the Saugatuck River, is open for its first spring and summer, ready to welcome guests with a variety of outdoor seating options, watching the boats and rowers go by. The restaurant will have an outdoor patio with seating for 40+ and an eight-person bar with water views, plus a second-floor dining deck off the main dining room offering what Dana Cifone, director of operations, says will be “intimate outdoor dining tables with elevated water views.” The Bridge’s main draw, however, might be its four unique riverside pergola cabanas featuring outdoor lounge-style seating, where patrons can enjoy the Bridge’s Golden Hour Tuesday through Friday from 4 to 6 p.m., featuring lite bites created by talented Executive Chef and partner, Stephen Lewandowski. Boaters will rejoice with The Bridge’s Dock & Dine option, which offers eight boat slips for guests to cruise up, dock, hop off and enjoy a lunch, dinner or a mocktail. Some of Cifone’s favorite drinks include the Private Plane—a bourbon, saffron amaro, spiced pear, brandy, Aperol, and lemon concoction—and the Westport Metro, made of rum, acid-adjusted pineapple and cava syrup.
4 Casa Me
This Italian eatery located downtown in Westport’s Sconset Square has become known around town not only for its delicious dishes of homemade pastas, farm-fresh veggies, and grilled meat and fish dishes, but also for its beautiful and stylish bar—which the restaurant says is “dedicated to the craft of Italian cocktailing and spirits.” When the weather warms up, Casa Me opens its floor-to-ceiling doors and windows, connecting patrons to the outside in a way that makes you feel like you’re in a little Roman café or perhaps in a village along the Amalfi Coast. Italian-inspired menu faves like apertivi, Negronis, spritzes, espresso martinis, and a selection of amari are all available, plus a carefully curated wine list from small family-owned Italian vineyards. Moreover, the restaurant offers a comprehensive mocktail menu, with refreshing non-alcoholic options including favorites like the Menta Be—a refreshing blend of cucumber, lemon, mint and soda and the Sicilian Sunrise—blood orange cordial, lime and soda. If you’re asking me—while you’re there—make sure you grab a plate of the Mafaldine al Limone—a lemony plate of deliciousness that’s one of the best pasta dishes I’ve had outside of (possibly even in) Italy.
5 The Clubhouse Rooftop Bar
The Clubhouse, which opened its doors this winter, recently revealed their own rooftop bar and restaurant in April. This fun, seasonal addition comes complete with fire pits, picnic tables, two cornhole sets, and three outdoor TVs for premium viewing of all the spring and summer sporting events. The rooftop offers the full food and beverage menu, plus some seasonal additions like frosé and fresh mocktails. Whether gathering for a casual afternoon with friends or enjoying an outdoor date night, the rooftop offers a lively yet laid-back setting perfect for any occasion. While you’re there, sign up for some of the restaurant’s other indoor offerings—like sports simulators, darts, and karaoke.