The Connecticut Shoreline

Westbrook Inn Blog

TOP 10 THINGS TO DO ON THE CONNECTICUT SHORELINE THIS SUMMER

The Connecticut Shoreline is the place for a New England summer getaway without the crowds. Visit Westbrook and its neighboring coastal towns—Old Saybrook, Chester, and Clinton—for a quintessential small-town escape. Whether you’re craving sun-soaked beaches, fresh-caught seafood, cultural experiences, or outdoor adventures, this region delivers. Here’s your guide to the top 10 2025 summer experiences that capture the best of this coastal haven.

Coastline Brewing Company

Catch a Show at The Kate

The Katharine Hepburn Cultural Arts Center, affectionately known as The Kate, is a cultural gem in Old Saybrook. This intimate venue hosts a vibrant calendar of concerts, theater, film screenings, and comedy shows, drawing both local and national acts. With over 67 concerts and events annually, from jazz to rock to classical, there’s always something to enjoy in this beautifully restored historic theater. Check the schedule and plan your evening around a performance for a true taste of the shoreline’s artistic spirit.



Surfridge Brewery Bar

Stroll the Chester Farmers Market

Every Sunday, the heart of Chester transforms into a bustling farmers market. Local growers, bakers, and artisans gather to offer fresh produce, homemade treats, flowers, and crafts. This market is more than a place to shop—it’s a community event where you can mingle with locals, listen to live music, and sample the flavors of the Connecticut River Valley. Arrive early for the best selection and soak up the small-town charm.



Little House Brewery

Spend a Day at West Beach

West Beach in Westbrook is an up-and-coming shoreline favorite gathering spot, beloved for its soft sand, gentle surf, and panoramic views of Menunketesuck, Duck, and Salt Islands. The largest of the town’s sandy beaches offers supervised swimming, a pier, picnic areas, and seasonal food concessions. Whether you’re sunbathing, swimming, or watching a fiery sunset, West Beach is the perfect place to relax and enjoy the Long Island Sound. Pro-tip: add a luxury beach picnic to your Westbrook Inn Bed & Breakfast stay for an upgraded beach experience.


Alternatively, a stroll in Hammonasset Beach State Park is always beautiful.

Surfridge Brewery Bar

Dinner at Charter Oak Tavern

After a day of exploring, head to Charter Oak Tavern for dinner. This new local favorite has a welcoming atmosphere and creative menu, featuring locally sourced ingredients and inventive New American cuisine. Pair your meal with a craft cocktail or a selection from the impressive wine list for a memorable evening out. If you are in the mood for a burger, their burger is amazing!


Little House Brewery

Savor Lobster at Lobster Landing

A Connecticut shoreline town visit is incomplete without a classic lobster roll, and Lobster Landing in Clinton is the place to get it. This waterfront shack is a legend, serving up hot, buttered lobster rolls that draw rave reviews and loyal crowds. The menu is simple—lobster rolls, chowder, and a few sides—but the flavors are unforgettable. Grab a picnic table by the water and savor the taste of the sea.



Surfridge Brewery Bar

Cocktails at Baccari Social

For a sophisticated nightcap, make your way to Baccari Social. This stylish cocktail lounge offers inventive drinks and a chic ambiance, perfect for unwinding after a day of sightseeing. Whether you prefer a classic martini or a creative house specialty, Baccari Social’s expert bartenders have you covered.



Little House Brewery

Shop the Boutiques of Old Saybrook

Old Saybrook’s Main Street is lined with charming boutiques, antique shops, and galleries. Spend an afternoon browsing for unique gifts, coastal décor, and stylish apparel. The town’s shopping district blends historic architecture with modern flair, making it a delightful place to stroll, shop, and people-watch.



Little House Brewery

Kayak the Patchogue River

For a peaceful outdoor adventure, paddle a kayak down the Patchogue River. The river winds through salt marshes and estuaries, offering excellent birdwatching and a chance to experience the region’s natural beauty up close. Many local inns, including the Westbrook Inn Bed & Breakfast, offer complimentary kayaks for guests. Glide along the water at sunrise or sunset for a truly magical experience.



Little House Brewery

Hike Gillette Castle State Park

Just a short drive inland, Gillette Castle State Park offers a unique blend of history and hiking. The park’s centerpiece is the whimsical stone castle built by actor William Gillette, perched high above the Connecticut River. Explore the castle’s quirky architecture, then hit the wooded trails for sweeping river views and a taste of Connecticut’s rugged landscape.



Little House Brewery

Explore Mystic: Seaport Museum, Aquarium, and Downtown

A trip to the shoreline isn’t complete without a day in Mystic. The Mystic Seaport Museum is the nation’s leading maritime museum, featuring historic ships, a recreated 19th-century village, and hands-on exhibits. The Mystic Aquarium is home to beluga whales, sea lions, and interactive marine displays. Afterward, stroll downtown Mystic for boutique shopping, riverside dining, and the iconic drawbridge. It’s a full day of discovery for all ages.



Little House Brewery

Where to Stay: Westbrook Inn Bed & Breakfast

Book a stay at the Westbrook Inn Bed & Breakfast for the perfect home base. This beautifully restored 1876 Victorian inn sits on the banks of the Patchogue River and is just a short walk from West Beach. Guests rave about the inn’s vintage charm, modern amenities, and warm hospitality. Enjoy a gourmet breakfast each morning, relax in the gardens or by the firepit, and take advantage of complimentary bikes and kayaks for exploring the shoreline. With its central location, you’re minutes from all the region’s top attractions and dining.

“The Westbrook Inn is so charming and welcoming… The bed was super comfortable, and the sheets ever so soft… There are also kayaks for use on the river, a small dock and outdoor fire pit. We took bicycles for a short ride to the beach—less than a mile.”

Plan Your Connecticut Shoreline Getaway

From the arts and culture of Old Saybrook to the sandy stretches of West Beach, the culinary delights of Clinton, and the maritime history of Mystic, the historical shoreline is the heat of summer destination that invites relaxation and adventure in equal measure. Make the Westbrook Inn Bed & Breakfast your retreat, and discover why this corner of New England is a favorite for travelers seeking authentic charm, natural beauty, and unforgettable experiences.

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