New England's Fairytale Town Is A Timeless Connecticut Gem With Riverside Ferries And A Cute Main Street

New England has no shortage of charm. Brimming with quaint coastal towns with beaches and cute cottages like Branford and adorable towns full of antique shops and serene scenery like New Hartford, Connecticut, in particular, boasts some of New England's coziest, most alluring destinations. Nestled along the Connecticut River between New Haven and the laidback scenic coastal town of Mystic, Chester is a timeless hidden gem with much to be discovered.

Offering a quintessential New England retreat, the town's cute Main Street is perfect for a relaxing day of shopping and dining, lined with boutiques, art galleries, cozy cafes, and delicious eateries. There's plenty to explore just beyond town as well, making Chester a perfect home base for delightful day trips. Hop aboard the local ferry for a magical journey across the Connecticut River to a fairytale castle, venture to a historic opera house for a night of musical theatre, and — in true New England fashion — end your day by settling into a charming Victorian-style inn. In Chester, the fantasies are boundless.

Situated about 30 miles south of Hartford and about 45 minutes from Windsor Locks, Chester is easily accessible for those who fly into Bradley International Airport (BDL). Since there's nothing more idyllic than a leisurely drive through New England, rent a car to reach Chester — though you won't need it much when you get there. Centered by a small, picturesque Main Street, Chester's cozy downtown district is a walkable hub of activity. Start your day by fueling at Simon's Marketplace, a quaint cafè in the heart of downtown serving fresh-baked pastries and hot espresso drinks. Next, stroll down the street to explore an array of local shops, including trendy fashion boutiques like Amber & Lowell and vintage treasure troves like The Little Shop by Nora Murphy Country House. Whether you're in the market for wall decor or you're just window shopping, there are several art galleries to check out. Admire local Impressionist oil paintings at the Leif Nilsson Spring Street Studio and peruse a mix of paintings, drawings, and sculptures at the Chester Gallery.

After you've worked up an appetite, sink your teeth into a savory, wood-fired pizza at OTTO Pizza, which pairs its pies with a selection of local beer and wine. If you're extra thirsty, head to Little House Brewing Company, a beloved brewery and taproom tucked into a 200-year-old historic haunt. Their tap menu is always rotating, offering sweet seasonal flavors like Apple Cider Donuts and Chocolate Bunnies. For classic pub fare, head to The Pattaconk 1850 Bar & Grille and choose from a hearty menu that features mouthwatering burgers, hot dogs, and seafood entrees. Save room for dessert, as Honeycone Craft Ice Cream serves scrumptious scoops of homemade ice cream with vegan options as well.

For a fairytale adventure, embark on a ferry ride to a real-life castle. Transporting travelers since 1769, the Chester-Hadlyme Ferry route cruises on a five-minute voyage across the Connecticut River, leading to Gillette Castle State Park. Shrouded in enchanting woodlands, the park's focal point is a modern medieval stone edifice dating back to 1914 built by former Sherlock Holmes actor and playwright William Hooker Gillette. Perched on a hill towering 200 feet above the river, the castle offers magnificent views from the top, and the park is free to wander during daylight hours. To explore the stunning 24-room fortress, self-guided castle tours are available for $6, and can be purchased in advance.

Before crossing the river back to Chester, complement your castle journey with a visit to East Haddam, a hidden fairytale town that offers an authentic slice of New England. The town's star attraction is the Goodspeed Opera House. Tucked into a beautiful historic building, the renowned theatre has produced over 250 musicals — 21 of which have made their way to Broadway — and has been honored with two Tony Awards for its contributions to American musical theatre. Be sure to check the calendar before your visit and snag a ticket to their current stage production for a dazzling evening of song and dance.

While you won't find lodgings directly in Chester, there are plenty of nearby accommodations to choose from. Settle into the idyllic Boardman House Inn Bed & Breakfast in East Haddam, or head back across the river to the Copper Beech Inn (about 5 miles south of Chester), which offers elegant rooms in a Victorian-style homestead for a classic Connecticut retreat.