Aspen Restaurant serves contemporary American cuisine with global flair, earning repeated accolades as one of the best new dining spots in the area. Located on Main Street in Old Saybrook, this elevated eatery serves fine dining meals made with fresh local ingredients.

The two-story Penny Lane Pub offers hearty English pub classics like fish and chips and shepherd’s pie, paired with a world-class beer list and nightly specials. With live music on Fridays and cozy spaces both indoors and on the patio, it’s a local hangout for casual dining with personality.

A waterfront favorite along the Connecticut River, Liv’s Shack serves hot buttered lobster rolls under a breezy tent. This BYOB, pet-friendly spot is summer dining at its most relaxed and tastiest, with gluten-free options as well.

Ashlawn Farm Coffee is a beloved local hangout serving cold brew, handcrafted espresso drinks, and gluten-free baked goods in a cozy, rustic setting. With outdoor seating, intimate indoor nooks, and strong Wi-Fi, it's ideal for both slow mornings and creative work sessions.

Dagmar’s Desserts serves authentic sweets, where locals enjoy everything from Austrian Linzer tortes to German marzipanstollen to French pastries. It’s a must-visit for dessert lovers craving Old World European flavor and artisan craftsmanship.

For go-to gourmet Italian takeout, Pasta Vista offers generous portions of pasta, soups, salads, and freshly baked bread. Great for feeding a family or stocking up on leftovers, the flavorful variety of vegetarian and traditional options make this a local takeout treasure.

Gain hands-on experience with Montauk Wild Oyster Shucking and learn proper techniques with provided gloves and tools. Guests enjoy freshly shucked Montauk wild oysters topped with classic condiments during this interactive experience near the Nature Conservancy.

Step back in time at Mystic Seaport Museum Adventure, a maritime gallery with blacksmith demos and a recreated seafaring village. Pre-booked admission gives guests self-guided access to immersive exhibits and insightful chats with on-site historians.

Uncover the haunted history of Mystic and nearby Stonington on this eerie Downtown Mystic Ghost Tour that blends supernatural tales with colonial-era history. Guided stops include Mystic River Park, the Bascule Bridge, and other sites with a chilling past.

Board the Private Hands-On Sailing Adventure in Montauk for a scenic cruise, where guests can relax or learn how to trim sails and take the helm. This hands-on excursion also includes views of Montauk Harbor and the surrounding Block Island Sound.

Explore the legacy of a legendary actress at the historic Katharine Hepburn Cultural Arts Center, lovingly called The Kate. With live performances and curated museum exhibits of personal memorabilia, it’s a must-see for film buffs and culture lovers alike.

Soar 350 feet above ground from the rooftop of Fox Tower on a thrilling HighFlyer Zipline at Foxwoods. Ending at the Mashantucket Pequot Museum, this attraction offers a flight with panoramic views stretching to Long Island Sound.

Recharge at Bliss Spa Old Saybrook with luxury treatments like massages, facials, reflexology, detox treatments, and contouring services at this serene spa retreat. It’s great to unwind after a day of exploring the beautiful coast of Connecticut.

Bring culinary magic home with Zavory’s Cooking Class led by Chef Aerin Zavory, a Chopped and Beat Bobby Flay champion. This three-hour, in-home experience blends expert instruction with fun, seasonal menus, perfect for gatherings or foodie date nights.