Fairfield County is officially in its golden hour—sun-kissed days, breezy nights and plenty of ways to max out your summer joy. Whether you’re in it for the salty hair vibes or the rooftop toasts, we’ve rounded up 10 must-do activities that deserve a spot on your summer bucket list.
1. Relax at Sherwood Island State Park
As Connecticut’s first state park, Sherwood Island in Westport offers sandy beaches, picnic areas and scenic walking trails. It’s an ideal spot for sunbathing, swimming or enjoying a family picnic with views of Long Island Sound.
2. Sip Craft Brews at The Beer Garden at Shippan Landing
Located right on the water in Stamford, The Beer Garden is an outdoor oasis with craft brews on tap, a rotating lineup of food trucks, live music and weekend vibes that don’t quit. Perfect for post-beach hangs, dog-friendly days and sunset selfies.
3. Bet on a Duck at Westport’s Great Duck Race
Thousands of rubber duckies. One 160-foot waterway. And a whole lot of fun. The Westport Sunrise Rotary’s annual Great Duck Race on June 28 is part fundraiser, part spectacle and full-on wholesome summer tradition. Buy a duck, cheer it on, and maybe win a prize—all while supporting charities near and far.
4. Pig Out on Art in Stamford Downtown
Need a family-friendly activity with a twist? Go on a walking pig hunt! Stamford Downtown’s interactive sculpture exhibit “Oink!” features 26 larger-than-life fiberglass pigs, all designed and painted by local artists. They’re scattered throughout downtown, making it the perfect excuse to stretch your legs, snap some pics, and say “hey” to a few artistic swine. Bonus points if you spot them all.
5. Sunset Sips at The Lobster Bin
Over in Greenwich, The Lobster Bin is the hidden gem that locals love for laid-back seafood feasts and chill outdoor vibes. Snag a seat on the patio, dig into a classic lobster roll or fried clam plate, and toast to summer with a crisp glass of white or local brew. It’s giving New England coastal in the best way.
6. Catch King Lear at Shakespeare on the Green
Swap the zoo for the bard! From July 10–20, Curtain Call in Stamford is staging King Lear outdoors at Sterling Farms. Bring a blanket, your favorite snacks, a bottle of wine (yes, it’s BYOB), and settle in for an evening of Shakespeare under the stars. Don’t worry if you don’t totally follow the prose—just nod thoughtfully and soak up the drama.
7. Shell-ebrate at the Norwalk Oyster Festival
Happening September 5–7, the Norwalk Oyster Festival is a beloved end-of-summer bash with fresh seafood, live music and family-friendly fun. From shucked oysters to carnival rides, it’s a must for foodies and festival-goers alike.
8. Celebrate July 4th at Jennings & Penfield Beaches
Fairfield goes all out for Independence Day with fireworks over the Long Island Sound. Grab your blanket, pack a picnic, and head to Jennings or Penfield Beach for one of the most scenic (and spirited) July 4th shows anywhere.
9. Feast at the Hey Stamford! Food Festival
If you love good food (and who doesn’t?), the Hey Stamford Food Festival is a must. Held annually in late summer, this foodie paradise brings together top local restaurants, food trucks, live music and more—all in one place. It’s a flavor-packed weekend you won’t want to miss.
10. Explore the Bartlett Arboretum & Gardens
Located in Stamford’s backyard, the Bartlett Arboretum & Gardens is a serene escape into nature. Whether you’re strolling through colorful blooms, sweating it out on a trail or simply relaxing under a shady tree, this hidden gem offers a peaceful retreat for nature lovers and families alike.