1. SPRITZES FOR SUMMER
You can find unique twists on this Italian staple of warm-weather months at spots like Felice, where their menu includes the Bianco Spritz which has fresh lemon juice, Italicus (a bergamot liqueur known for floral sweetness), Strega (for subtle notes of mint, juniper, and fennel), and a cucumber and mint garnish. “We love how each spritz expresses the season’s freshness through its own story,” says Elvis Aguirre, Felice’s bar operations manager. Over at Massi Co., “The Summer of Spritz” is in full effect on their newly-opened Post Road patio. Beverage director Nico Rainey-Ray brought over small-batch Italian liqueurs like Aspide, a Sardinian aperitivo made from wild herbs and bittersweet citrus, and Nepeta, a Sicilian amaro distilled from wild calamint and sun-dried lemon, to their bar program. You’ll also find produce-centered beverages tied to summer's pinpoint-specific peak freshness, like strawberries in June, figs in August, and house-grown gooseberries. There's not a bad one in the lineup (pictured), and there’s no surer sign that summer has arrived than that first sip.
2. WESTPORT'S WINNINGEST BITES
Each year, the Westport-Weston Chamber of Commerce polls residents for their favorite eats in a given category; this year’s was sandwiches. The crowned winners included the chicken sandwich from Garelick & Herbs, the combo sandwich from A&S Fine Foods, and the NY Deli sandwiches from Gold's Delicatessen—any of which would be perfect for a packed lunch at Compo—but you could spend a whole summer eating your way through their previous winners, which include classic burgers from Shake Shack, cheese pizza from Pizza Lyfe, and vegetable soup from Organic Market.
3. OUTDOOR DINING
There are too many great sun-soaked spots to count: there’s the eateries on Church Lane like Spotted Horse, Pink Sumo, and The Blondinit that spill into the streets and feature live music on weekend evenings. There are the first-timer outdoor spaces, at new spots Massi Co. and Felice. "Railroad Place is the go-to place for al fresco dining in the summer. Four restaurants; Tarantino’s, Blu Olive, Romanacci and Allium are all lined up,” says Matthew Mandell, the executive director and president of the Westport-Weston Chamber of Commerce.
There are sweeping river views at The Bridge at Saugatuck. “Outdoor season at The Bridge is really where everything comes together," says Stephen Lewandowski, The Bridge's managing partner and executive chef. "You have this balance of crafted New England cuisine, sunset views, and that coastal air that just shifts the mood.”
At The Whelk, the recently renovated waterfront patio has fire pits and a new “Oysters & Rosé on the River” pairing, featuring local oysters from Copps Island in Norwalk and dry, mineralic Château Les Valentines rosé from Provence. (The Whelk is the only restaurant in Westport with that particular wine.) It’s just hard to have a bad time when you’re dining al fresco in Westport.
4. THE LEVITT PAVILION
Westport’s only all-outdoor music venue offers more than 50 free shows under the stars each season, and this year’s lineup is another stellar one (pun intended). “We are bringing back favorites and deepening relationships with artists, and we are also bringing in new voices from all over the world,” says Carleigh Welsh, the vice president and executive producer at the Levitt Pavilion for the Performing Arts. This month, there's a two-night residency from returning favorite The Disco Biscuits on June 12 and 13, an appearance from the jam-rocking Rolling Together Revue Tour (which features G. Love, Donavon Frankenreiter, and Moon Taxi) on June 23, Greensky Bluegrass on June 11, Lucius on June 20, and Dark Star Orchestra on June 21. Plus, here’s a look at what else is coming up this summer. For tickets and more info visit levittpavilion.com
MATTEO BOCELLI
On July 10, the Levitt Pavilion presents Matteo Bocelli’s Falling In Love World Tour. Matteo is the son of world-famous tenor Andrea Bocelli, but his sound is all his own, blending modern pop production and classical Italian techniques. His music couldn’t be a better match for summer: think Tuscan vineyards and “la dolce vita” on a moonlit Westport night.
JAZZ ALL SUMMER
2026 marks the sesquicentennial of the U.S. (that’s the 250th birthday), and the Levitt is celebrating with jazz shows all summer. “There’s a beautiful jazz through-line all season—it’s a unique American art form, and an exciting way to celebrate,” says Carleigh. In fact, the season kicks off with Charlie Hall and the Get Up With It tribute to the Miles Davis Centennial on May 24, and continues with a free show from Jumaane Smith on June 7, and Jazz at Lincoln Center Orchestra with Wynton Marsalis on June 28.
FAMILY-FRIENDLY SHOWS
Every Wednesday night, the Levitt hosts kid and parent-approved concerts. “Our children’s series features Grammy-award winning artists who are enjoyable for ears of every age,” says Carleigh. “It’s an opportunity to bring children of all ages to shows and introduce them to all sorts of music and art forms.” And they’re completely free shows. “The premise of them being free is to be an invitation to discover, explore, and make active listening a part of daily life.”
5. THE WESTPORT COUNTRY PLAYHOUSE
The venerable theater, now in its 96th season, used to primarily be a summer institution, acting as a seasonal home base for N.Y.C.-based performers and artists who spent June-September in Westport. These days, there’s hardly an off week, but that doesn’t make summers at WCP any less special—just look at this lineup. For tickets, showtimes, and more, visit westportplayhouse.org
FAMILY SHOWS
The youngest Westporters shouldn’t miss the return of Pinkalicious The Musical, based on the beloved picture books by Westporter Victoria Kann, on June 7. And animal lovers of all ages will enjoy the tour of Mutts Gone Nuts, a high-energy show of incredibly talented dogs and their most impressive tricks, rolling through Westport on June 21.
MAINSTAGE SHOW
Closing out the WCP’s 2025/2026 season is their production of Agatha Christie’s The Murder of Roger Ackroyd, adapted for the stage by the Playhouse’s artistic director, Mark Shanahan. The show is the quintessential mansion murder mystery, full of twists, turns, and masterful moments. It’s a perfect summer night out. It runs July 14-August 1.
SPECIAL EVENTS
Judy Garland would turn 104 on June 10, and to celebrate, Jenna Pastuszek is bringing her show, Get Happy! Celebrating 100+ years of Judy Garland, which features songs from The Wizard of Oz, Easter Parade, The Judy Garland Show, and more, to the Westport Country Playhouse on June 17. The Playhouse also hosts its third annual golf tournament—featuring canasta and mahjong for the less links-inclined!—at Birchwood Country Club on June 15. And there are more cabarets, concerts, and events still to be announced—check westportplayhouse.org early and often.
6. TASTING STATIONS
On Wednesday, June 3, the 20th annual Taste of Westport offers diners a chance to sample bites and drinks from some of the area's top restaurants. The event benefits CLASP Homes, which helps provide group homes and round-the-clock services for adults with autism and developmental disabilities. This year's Taste is at the Fairfield County Hunt Club; for tickets and more information, visit tasteofwestport.com And later this summer, catch the 14th annual Slice of Saugatuck Festival, billed as a “food tasting and retail experience,” features dozens of restaurants, shops, and galleries along Riverside Avenue, Railroad Place, and Saugatuck Avenue sharing samples and good vibes. There’s live music, activities for kids, and of course, plenty to eat. Sponsored by the Westport-Weston Chamber of Commerce, this year’s festivities happen on Saturday, September 26. For more information and participating vendors, visit westportwestonchamber.com
7. THE SOUNDVIEW SUMMER STROLL
Dan Woog (see page TK) instituted this tradition in 2024, a collaboration between his site 06880 and the Compo Beach Improvement Association. The Summer Stroll closes off a stretch of Soundview Drive to vehicle traffic and fills the street with live music, kids’ activities, food stations, and “a fun community vibe.” This year’s stroll will be on July 26th, from 10 a.m. to 3 p.m., so save the date.
8. THE SIDEWALK SALE
Downtown Westport comes alive in the summer, and one of the best shopping weekends of the year is the annual Sidewalk Sale, sponsored by the Westport Downtown Association. From June 26 through the 28, from 10 a.m. to 5 p.m., you’ll find deep discounts all along Main Street, and not just from stores—select salons, fitness and wellness studios, and more local favorites also participate. For more information, visit westportdowntown.com
9. THE FIREWORKS
Described by many Westporters as “the best night of the year,” the 2026 PAL Independence Day Fireworks Celebration, generously sponsored by Melissa & Doug Bernstein and the Bernstein Family Foundation, will light up the skies on July 2, with a rain date of July 3. Passes, which go on sale June 1 at the Westport Police Department (50 Jesup Rd) and June 3 at the Parks and Recreation Office (260 Compo Rd. S), are cash or check only, and parking spots start disappearing around 5 a.m. on the day of the show. But it’s worth the sacrifice to be on the beach for this magical night.
10. THE YANKEE DOODLE FAIR
The Fair is a “Westport institution,” and for good reason: the annual weekend, running from Thursday, June 18 through Sunday, June 21, features carnival rides and games, classic fair food from both the food court and the WWC’s bake sale, raffle prizes, and happy kids of all ages. The Yankee Doodle Fair is a major source of funding for the Westport Women’s Club’s philanthropic programs, including local grants and need-based scholarships for Staples seniors. For more information, visit westportwomansclub.org
11. THE WESTPORT FARMERS MARKET
Yes, you can shop the WFM ten months out of the year, but there’s something special about the transition, on May 7, from the indoor Gilbertie’s location to the 50 Imperial Avenue blacktop. And this is an especially-special year: the market is celebrating its 20th anniversary, a rare milestone among farmers’ markets. “We’re grounded in staying authentic and serving our community,” Lori Cochran-Dougall, the executive director of the WFM, says of the market’s longevity. Every Thursday from 10 a.m. to 2 p.m., you’ll find delicious, sustainable vendors (most of which you can’t shop anywhere else), including five new-for-2026 ones, like Rudeboy Baking Co. and Black Girl Kimchi. “I want you to walk through the market and just feel like ‘this place loves me,’” says Lori. On behalf of shoppers all over town: mission accomplished.
12. COMPO BEACH
Westporters are immeasurably lucky to have Compo Beach in our literal backyard: whether you're barbecuing, enjoying the playground, or just lounging with a good book, it's always a wonderful place to spend a warm, happy day. To best enjoy it, though, you want to be prepared, so we're finishing off our summer guide with Compo-approved picks for beach gear, from dermatologist-recommended sunscreens to sand-friendly coolers, towels, and wagons. Now pack your bag and savor every moment of this special season.
13. DR. LAUREN LEVY'S SUNSCREEN PICKS
Dr. Lauren Levy is a board-certified dermatologist at Westport Dermatology & Laser Center who specializes in acne, rosacea, hair loss, and medical dermatology. She shared her favorite sunscreens with Westport Lifestyle for healthy, hydrated, sun-safe skin.
Best mineral for daily use: Eucerin Sensitive Mineral, SPF 35+
“This is my favorite for every day because the tint protects from blue light,” says Dr. Levy. “It’s especially good to use tinted if you suffer from melasma. The shade is just enough coverage to forgo heavy makeup in hot weather.” $20 at CVS
Best for daily use: EltaMD UV Clear
“It’s non-mineral and great for those with acne-prone skin. And it comes in tinted and non-tinted formulations.” $45 at Bluemercury
Best if you have redness/rosacea: EltaMD UV Skin Recovery SPF 50
“This is a lightweight daily sunscreen for those prone to facial redness or impaired skin barrier, with ceramides to repair and soothe the skin. It even comes in a green-tinted version for those who suffer from severe facial redness.” $52 at Bluemercury
Best face stick: Neutrogena Ultra Sheer Face Stick, SPF 60
“Easy application and does not leave a white paste. It’s great for kids at camp, or to keep in your bag for a mid-day reapply.” $15 at CVS
Best body spray: EltaMD UV Aox Mist, SPF 40
“I prefer a mineral spray sunscreen, rather than a chemical spray,” she says. “This one has a sheer finish, antioxidants, and won't leave your skin pasty and dry.” $46 at Bluemercury
Runner up: Sunbum Mineral Sunscreen Spray, SPF 50
“It is a little thicker than the Aox, but it really holds up in the water. Great for long beach days.” $22 at CVS
Best lip sunscreen: Colorescience Peptide Lip Shine, SPF 30
“It keeps lips hydrated and has several different shades to choose from. And no sunscreen taste!” $31.50 at target.com
Best scalp sunscreen: Coola Scalp and Hair Sunscreen Mist
“It’s a non-greasy spray that protects your part from burns.” $30 at Ulta
Best preventative: Inner Glow Sol Defense Gummies
“Taking two gummies one hour before sun exposure helps your skin fight free radical damage,” Dr. Levy explains. “It contains Polypodium Leucotomos and niacinamide, which can help prevent sun damage. Studies show that taking these gummies prior to sun exposure can reduce your chance and/or intensity of burn. My whole family takes them every day during the summer and high sun exposure days. They taste delicious.” (Just use regular sunscreen, too!) $32 at amazon.com
Dr. Levy graduated from the Mount Sinai School of Medicine and did her residency at Yale's Department of Dermatology. She is the author of numerous publications and editor of a popular dermatology board review textbook. Her hobbies include spending time with her children, Pilates, and watching Bravo.
14. THE VERY BEST BEACH GEAR
Tested by our editor, Sara Gaynes Levy, who also road tests family-friendly products for outlets like PEOPLE, The Strategist, and Babylist
Veer City Cruiser Wagon, $699, potterybarnkids.com
Every time my husband brings this wagon to Compo Beach, someone stops him to ask where he got it. Yes, it's pricey, but it's 10 times more durable than the flimsy pop-open wagons—the tires can actually maneuver on the sand, and the optional add-on canvas shades ($19 each) give our kids a shady place to picnic if the sun gets too strong.
Spielstabil Ice Cream Duo, $15 at Nordstrom
I always have this ice-cream-themed sand toy set in my beach bag—it takes up almost no room, and everyone loves playing "ice cream shop" along the Compo shores. (Pro tip: I've also spotted these at The Toy Post on the Post Road!)
Yeti Tundra Hall, $450 at Williams-Sonoma
We bring this cooler to Compo constantly: it fits tons of stuff, keeps things impressively cold (don't sleep on the Yeti-branded accompanying ice packs, $25 each, for when you forget to buy ice), and has extra-sturdy wheels for dragging into the sand. I love the handle, which tucks away but provides impressive turning leverage, and the spigot for draining when the party's over.
Portable Cornhole Set, $250, thetwoohthree.com
I love this local brand, and their portable cornhole set is just too fun. The genius design packs up like a suitcase, and the bean bags sit in built-in storage pockets. It's an all-in-one good time, too: the set includes two boards, bean bags, internal storage, and dual scorekeepers.
Bathing Culture Cosmic Rainbow Organic Body Towel, $88, revolve.com
How cute are these ultra-absorbent beach towels? They're made from organic cotton, so soft and plush, and dry quickly. I also adore the happy, bright colors and the way they stand out on the sand: you'll never lose your spot!
Yeti Trailhead Camp Chair, $300, yeti.com
The best chairs ever, of all time. They collapse neatly into wearable backpacks. They open so easily you can do it one-handed. They have built-in cupholders. The seat is high enough that it's not a chore to get in and out of them. Simply a 10/10 purchase.
L.L. Bean Boat and Tote Zip-Top, $65, llbean.com
It's a classic for a reason. I've had many other beach and pool bags over the years, but I always come back to this one. It's seemingly indestructible, always bounces back from getting splashed or covered in sand, and holds everything. Splurge to get it monogrammed so you know it's yours, and definitely get the extra-long handles!