Essex, Connecticut: Antique train at Essex Train Station.

10 Picture-Perfect Towns in Connecticut

Taking pictures has become a quintessential part of travel, new experiences, and significant events. Pictures with friends, with family, or with pets, by using a selfie stick, a tripod, or asking a stranger for help. Everyone is fond of those picture-perfect moments. However, even more important than how you take a picture is where you take it. These days, few can experience a breathtaking and exciting environment without taking a moment to share the experience with those they love most. The state of Connecticut is full of such destinations. Destinations that are full of charm, beauty, history, and gorgeous landscapes. Picture perfect locations that are sure to leave lasting impressions that you will remember for decades to come.

Essex

Essex, Connecticut: Waterside houses among trees with boats moored to wooden jetties on a clear autumn day along the Connecticut River.

Essex, Connecticut: Waterside houses among trees with boats moored to wooden jetties on a clear autumn day along the Connecticut River.

As you drive into one of the most beautiful towns in Connecticut you will be instantly captivated by its charm. Home to the historic Griswold Inn, the oldest continuously operated inn in the United States, that old town feel is not in short supply in Essex. It is ideal for both photographers and social media influencers interested in showing off a little more culture. The town features the Pratt House, a well-preserved 18th-century home, and The Connecticut River Museum showcases local river history. You can also enjoy the Essex Steam Train and Riverboat, which offers a combined train and boat journey. The town happens to be a site of much historical significance from events as far back as the War of 1812 when British troops attacked the town. Essex hosts the annual "Trees in the Rigging" boat parade on the Connecticut River. Opportune for fishing and boating or just picnics on its river banks. Kayaking and canoeing are also recommended. It is a gorgeous country with very clean water, but keep an eye on the weather because the river can go from a trickle to a torrent very quickly.

Mystic

Mystic, Connecticut: Mystic Seaport, outdoor 19th-century village and maritime museum with wooden vessel docks.

Mystic, Connecticut: Mystic Seaport, outdoor 19th-century village and maritime museum with wooden vessel docks. Editorial credit: Faina Gurevich / Shutterstock.com

Mystic goes beyond picture-perfect, delivering a backdrop that is unmatched by practically any destination in the country. The Annual Mystic Outdoor Art Festival attracts artists and visitors nationwide. The twin's natural features like the river and nearby forests are awe-inspiring and at night under the gleam of stars and moonlight as magical as the town's name implies. Olde Mistick Village, an outdoor shopping center that replicates a 1720s New England village, combined with Mystic Pizza, the inspiration for the movie of the same name, is perfect for social media lovers wanting to add something special to their profiles. The historic drawbridge spans the Mystic River and is frequently raised for boat passage, giving a unique background for photos. The Mystic Aquarium includes beluga whales and offers interactive exhibits. The town of Mystic is a water lover's dream and delivers scenes that only beautiful waterfronts can deliver. In Mystic, one can find genuinely Instagram-worthy moments that make a weekend getaway more than worth it.

Kent

Kent, Connecticut: Early autumn at Macedonia Falls State Park.

Kent, Connecticut: Early autumn at Macedonia Falls State Park.

Likely to be one of the most well-known Connecticut towns, Kent is a common stop for anyone traveling by the Appalachian Trail. Its beautiful forestry views, with babbling brooks and mountainous horizons, transport visitors to an elven fantasy land. It's the type of environment read only about in books. Kent Falls State Park features a series of waterfalls on the Housatonic River that are refreshing and rejuvenating. A perfect destination for painters and photographers searching for excellent landscapes or to capture the true essence of nature. Kent’s history and its connection to nature are its beauty. Kent's Art Barn showcases local artists in a rustic setting, and Bulls Bridge, one of the few functional covered bridges in Connecticut, is the background of many wedding, maturity, and family portraits every year. There is also the Annual Kent Pumpkin Run, a famous local road race that captivates the wonders and elegance of the fall season, when the entire town is transformed with breathtaking autumn leaves. 

Guilford

Guilford, Connecticut: Historic 1639 Rev. Henry Whitfield House and Museum, originally a protective fort and the minister's home.

Guilford, Connecticut: Historic 1639 Rev. Henry Whitfield House and Museum, originally a protective fort and the minister's home. Editorial credit: LEE SNIDER PHOTO IMAGES / Shutterstock.com

Gorgeous views are not in short supply in Guilford. It is a town steeped in American history dating back to the colonial era. There is the Henry Whitfield State Museum, the oldest stone house in New England, as well as the Hyland House Museum, depicting colonial life. Both offer great “let me take a selfie” moments and are perfect to take advantage of while visiting Guilford Green, a historic town center with numerous events and festivals. However, history is not Guilford's only charm. Chittenden Park offers beach access and views of the Long Island Sound picturesque and dreamy at sunset offering a truly romantic setting adding to its romantic charms is the Bishop's Orchards, a local farm and winery with seasonal events.

Chester

Chester, Connecticut: Winter festival tractor parade.
Chester, Connecticut: Winter festival tractor parade. Editorial credit: Joe Tabacca / Shutterstock.com

The range for picture-perfect moments in Chester is impressive. From tranquil images of historical artifacts to the high-energy scenes that only man's best friend can deliver. Chester is home to one of the oldest continuously operating ferries in the United States, Chester-Hadlyme Ferry. Adding to the historical charms of the town. The town boasts the Goodspeed Opera House, known for musical theater productions, and the Chester Museum at The Mill presents local history in a former factory. The Maple and Main Gallery features works from Connecticut artists that are inspirational and stir creativity. For outdoor lovers, there is Paddle Creek, a popular spot for kayaking and canoeing, and The Annual Chester Dog Fair, which celebrates local canine friends.

Old Lyme

 Old Lyme, Connecticut: Exterior of the Old Lyme Ice Cream Shoppe and Cafe, a local small-town business with unique decorations and outdoor seating on a spring day.
 Old Lyme, Connecticut: Exterior of the Old Lyme Ice Cream Shoppe and Cafe. Editorial credit: Rachel Rose Boucher / Shutterstock.com

This town is the perfect getaway for both history and art lovers and brings with it many selfie-worthy moments. Florence Griswold Museum, the home of American Impressionism, The Lyme Art Association, a historic artists' colony, continues to exhibit works that reach their peak during the Old Lyme Midsummer Festival, a celebration of arts, crafts, and music. The Sculpture Grounds feature over 100 outdoor sculptures that will leave your hands glued to your camera with much enthusiasm to capture every moment. A stay at the Bee & Thistle Inn is highly recommended. It is a historic inn with gardens and river views offering romance and a tranquil retreat. The Lieutenant River provides scenic kayaking and birdwatching spots that will leave memories that will never be forgotten. 

Wethersfield

Old Wethersfield, Connecticut: Chester Bulkley House
Old Wethersfield, Connecticut: Chester Bulkley House. Editorial credit: SMGarten / Shutterstock.com

Wetherfeild is home to Elizabeth Park, the oldest rose garden in the United States. That alone is reason enough to visit one of the most captivating towns in Connecticut. Wethersfield Cove offers more outdoor beauty by being a favored part of the Connecticut River, popular for boating and fishing, sunset walks, and picnics with friends or family. The Annual Cornfest celebrates local agriculture and community, perfectly capturing the spirit of autumn. There are also many opportunities to capture images of history by visiting the Broad Street Green at the heart of the historic district with its colonial architecture, or Webb-Deane-Stevens Museum, showcasing three historical homes sure to impress and create an envy to replicate their features with a modern twist back home.

Simsbury

Simsbury, Connecticut: The Old Drake Hill Flower Bridge, originally carrying Drake Hill Road over the Farmington River, is one of three surviving Parker truss bridges in the United States.

Simsbury, Connecticut: The Old Drake Hill Flower Bridge.

You cannot stop yourself from asking a nearby stranger to take a picture of you as you stand next to The Pinchot Sycamore, Connecticut's largest tree. Nature takes on new heights in Simsbury. There is Talcott Mountain State Park, home to the Heublein Tower with panoramic views that are breathtaking and awe-inspiring any time of the year. A visit to The Old Drake Hill Flower Bridge, adorned with over 72 flower boxes, will inspire impromptu photoshoots that will leave family and friends gasping with envy. Not to mention there are the Simsbury Fly-In featuring vintage aircraft and car shows that take place throughout the year. This town truly knows how to inspire picturesque moments. Simsbury Meadows Performing Arts Center and The Simsbury Free Library, a historic building with community programs, host concerts and events all year long, providing excellent reasons to spend a weekend taking in the sites and immortalizing the memories in social media. 

Stonington

Stonington, Connecticut: American flag blowing in the wind with a vintage car in the background in a small New England town.
Stonington, Connecticut: American flag blowing in the wind with a vintage car in the background in a small New England town. Editorial credit: Joe Tabacca / Shutterstock.com

Saltwater Farm Vineyard offers wine tastings in a converted World War II-era hangar and is transformative. The town of Stonington brings beauty and creativity together in a new way. Stonington Harbor Light, a historic lighthouse with museum exhibits, gives a time classic backdrop that inspires artists. It's an environment ideal for sea view lovers. DuBois Beach provides a relaxing coastal setting, and Stonington Borough's walkable waterfront with local shops and eateries creates the perfect weekend getaway for the family that will likely become a mandatory part of the annual family summer trip. The Captain Nathaniel B. Palmer House, home of a famous Antarctic explorer, will inspire young ones in a way that will have parents snapping constant photos to remember rare moments away from TV and computer screens. Stonington is the gift that keeps on giving. 

Madison

Madison, Connecticut: Blue hour after sunset view from East Wharf beach.

Madison, Connecticut: Blue hour after sunset view from East Wharf beach.

Home to Hammonasset Beach State Park, Connecticut’s largest shoreline park, Madison offers a little something for everyone. Between Sculpture Mile, an outdoor art exhibit featuring diverse sculptural works, and Bauer Park offers educational programs and walking trails outdoor photography becomes a must when visiting this town. There is the Madison Arts Cinema, a boutique theater showcasing independent and foreign films with a vintage feel as well as the Madison Historical Society which presents the town's history through multiple properties. That will inspire architecture lovers. Also, do not forget to plan a visit to RJ Julia Booksellers, an independent bookstore with author events and book lovers paradise.

Connecticut's Timeless Beauty

Picture-perfect memories are not always found in the impressive historical monuments of Europe. They can also be found in the simple life and quaint charms of many US cities. There is an art that only America’s forests and natural features can possess. Take a trip through Connecticut and explore the beauty of one of the United States’ oldest and most beautiful destinations.

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