A Small Town with a Rich Heritage

Introduction to Woodbury Ct

Live the small town life in Woodbury. Located in the Northwest hills of Litchfield County. Woodbury was founded in 1673 and is known for its distinctive town center. Instead of a center green or town center square, Woodbury’s historic center has numerous older buildings arranged linearly along both sides of Main Street.

Spanning approximately two miles, Main Street is lined with a variety of locally owned small businesses, shops, and restaurants, some nestled in plazas while others are beautifully restored antique homes. It is this very charm that led to Woodbury being named Connecticut’s “most charming small town” by Reader’s Digest in 2020.

Main Street

Woodbury’s Main Street also includes several public buildings that are in the National Register of Historic Places, such as the First Congregational Church (founded in 1817), Old Town Hall( erected 1845), United Methodist Church(founded in 1839), St. Paul’s Episcopal Church (founded in 1786), and North Congregational Church (founded in 1816 by members who had left the First Congregational Church of Woodbury). 

The most striking public building is the Masonic Temple. It is the oldest Masonic Temple in continuous use in Connecticut originally chartered in 1765 and built high on a rocky cliff on Main Street.

It is a modest, clapboard, Greek Revival temple visible from many points in town, especially when illuminated at night.

Woodbury is often referred to as Connecticut’s antique capital due to the presence of numerous historic houses that have been occupied by antique shops since the late twentieth century. The Woodbury Antique Dealer’s Association has a membership of current antique dealers who have some of the finest art, period furniture and collectibles. Even Martha Stewart has been known to shop here.

Location and Accessibility

Woodbury, nestled in the Pomperaug River valley, is a charming small town that offers a peaceful escape from the hustle and bustle of big cities. Despite its serene atmosphere, Woodbury is conveniently located just a short drive away from major cities like New Haven, Waterbury, and Hartford. This means residents can enjoy the tranquility of small-town life while still having easy access to the amenities and opportunities of urban areas.

Additionally, Woodbury’s idyllic location allows residents to explore and connect with other neighboring small towns such as Southbury, Washington, Roxbury, Watertown, and Middlebury. Living in Woodbury truly offers the best of both worlds. Plus, with its excellent highway connections including I-84, Route 8, and Route 6, getting to and from the town is a breeze.

If you’re looking for a peaceful getaway or the perfect mix of rural town living with the amenities of nearby city”s, Woodbury is a great place to live or visit.

Natural Beauty

Surrounded by rolling hills, lush forests, and numerous rivers, Woodbury offers breathtaking rural town landscapes. The natural beauty of Woodbury is awe-inspiring, especially during the fall season. The town’s rolling hills, dotted with Hay and Corn fields and surrounded by dense forests create a stunning backdrop with the vibrant fall colors. Woodbury is the exact opposite of big city life.

One of the best aspects of small town living is finding solitude. There are fewer people in smaller towns and there is a much slower pace of life. It gives you plenty of opportunities to connect with nature.

Parks and Trails

One of the more popular spots to take in this natural beauty is Orenaug Park. Home to over 200 acres of pristine wilderness, the park features several hiking trails, fishing spots, and a picnic area. At the Park Road entrance to the Orenaug trail, there are two pillars that are constructed of colorful stones from all 50 states.

The pillars are approximately 127 years old and received a major restoration in 2020. Follow the trail up to the Fire tower and enjoy the view west. Climb to the top of the tower if you dare. Afterward, hike down the backside of the trail and check out the Frisbee golf course. Check with the Park department for supplies if you wish to play and meet some new friends.

Flanders Nature Center

Once you’ve checked out Orenaug Park you’ll discover that Woodbury has so much more to offer. Woodbury boasts the Flanders Nature Center and Land Trust. It is a perfect place to explore and appreciate the beauty of New England throughout the year.

The Flanders Nature Center offers visitors a unique opportunity to learn about nature and its preservation. The center features hiking trails, an educational center, and a farm where you can pet and feed the animals.

Every spring you will see buckets attached to the many maple trees lining the streets here in town. For weeks you can watch or participate as volunteers continuously check and empty these buckets into a collecting tank usually on a truck or tractor. Then the collecting tank is brought to a central holding tank at the Flander’s sugar house where the magic of maple syrup happens. You can participate in all aspects of the process too. Check here for more info.

Water Company Land Purchase

One of the newer trails in Town the Trolley Bed Preserve, is located at the intersection of Old Sherman Hill and Trolley Bed Road off Route 64. The trail is part of the 248-acre Aquarion reservoir property the town acquired back in 2016. It’s a short trail that leads to an old reservoir pond. The trail centers around an old trolley bed trail that makes it ideal for walking.

If you’re a fan of kayaking, Woodbury is the perfect place for you. With several rivers and creeks running through the town, there are plenty of spots to enjoy kayaking. One of the most popular spots is the Pomperaug River.

Kayakers can enjoy a serene ride through the forests, taking in the beautiful scenery and wildlife. Another popular kayaking spot is the Shepaug River. The river boasts several beautiful waterfalls and rapids where kayakers can test their skills.

FARM LIFE in Woodbury Ct

In addition to its natural beauty, Woodbury is also home to many farms. The town’s rich agricultural history and fertile lands produce some of the best crops in the region. These farms offer visitors a chance to experience the charm of country living while enjoying the freshest produce.

Popular Farms

The most popular farms are The Farm, Woodbury, and Logues Farm. These farms provide seasonal produce and experiences such as strawberry picking, hayrides, sunflower festival, and pumpkin picking and they both have locations to pick up your fresh produce and groceries. Locals get so excited each summer towards the end of July for Logue’s sweet corn. I eat corn on the cob almost every day for as long as it shows up at our local Market. If you’re here this time of year be sure to try it. You never tasted anything better.

Education & Community

With strong public schools and close-knit community activities, Woodbury is a great place for families.

1. School System in Woodbury Ct

One of the major attractions for families in Woodbury is their top-rated public school system. Woodbury is a regional school district, which means the two towns of Woodbury and Bethlehem have joined together to provide education to the two towns. There are two K-5 schools, one located in each town. The middle school and high school are both located in Woodbury but service all the children in both towns. We also share a Board of Education.

Student to Teacher Ratio

Woodbury’s average student-to-teacher ratio of 12:1 so it’s no surprise that Woodbury’s schools have a great reputation for providing quality education. School rating services like GreatSchools.org and Niche give Woodbury schools an overall rating of 8 out of 10, with many schools receiving higher scores.

Nonnewaug High School offers an Agricultural Science and Technology Education (also known as vocational agriculture, or Vo-Ag). The Ellis Clark Regional Agriscience and Technology program was started by Ellis Clark at Woodbury High School in 1920.

It was the first of its kind in Connecticut until the vocational agriculture program that exists today was created by the Connecticut General Assembly in 1933 in order to offer this program on a statewide basis, From a small class of 11 boys that wanted to help their parents out on their family farms, the program has grown to more than 350 students that want to pursue different careers in agriculture.

Sports are a big part of the Woodbury community and Region 14 is part of the Berkshire League. The Berkshire League is made up of nine member schools from around Litchfield County. The schools tend to be smaller regional schools and the league encompasses all public schools from the county with the exception of New Milford, Torrington and Watertown.

All the schools in the Berkshire League are smaller towns and student-athletes tend to compete in multiple sports so you really get to know the athletes from all the schools. Living in small towns has many advantages, but one is that you can’t help but feel less animosity toward your adversaries.

You see them at the local coffee and ice cream places, work with them at the local shops and then play against them in multiple sports. It’s kind of why small-town residents have a better well-being than people from the big city – everyone truly is your friend.

2. Community Events in Woodbury Ct

Woodbury is known for its small-town atmosphere which is mainly due to its thriving community. There are many events all through the year that bring neighbors and families together.

One such event is the annual Christmas Festival, a two-day event that takes place on the first weekend of December and draws visitors from throughout the state.

Woodbury also boasts a volunteer group called Winter Lights of Woodbury which is dedicated to lighting Woodbury’s center of town, bringing joy & kindness during the holiday season.

There is also the Earth Day celebration held every year at Hollow Park, where community members can come together and enjoy environmentally-friendly activities.

And, of course, many more events throughout the year that you can check out here.

What sets Woodbury apart from other small towns is the charming stroll down Main Street. As you leisurely walk along, you’ll be greeted by the delightful sights and sounds of the community coming alive.

With each step, you’ll inevitably find yourself engaged in friendly conversations with fellow walkers, exchanging stories, and catching up on the latest community events. The lively atmosphere and sense of togetherness make this Main Street experience truly special, creating a lasting impression that will draw you back time and time again.

3. Parks and Recreational Opportunities in Woodbury Ct

For families that love the outdoors, Woodbury Ct offers a wealth of recreational opportunities.

Hollow Park is a natural haven for locals and visitors alike. This expansive, beautifully maintained park offers a plethora of activities year-round. Its vibrant green space, traversed by the Pomperaug River, poses a remarkable setting for peaceful strolls and hikes, catering to all fitness levels. The park also serves as the center stage for the annual fireman’s carnival, a cherished tradition featuring rides, games, and food, bringing the community together in a festive ambiance.

During the summer months, Hollow Park becomes a cultural hub presenting a series of concerts. These occasions allow residents and visitors to enjoy a variety of music genres while basking in the park’s idyllic surroundings. The Fourth of July is a particularly special time in the park, with a spectacular fireworks display that lights up the Woodbury sky, creating an unforgettable spectacle.

For the younger members of the community, Hollow Park provides a wide range of camps. These programs offer children an opportunity to engage in fun, educational activities, promoting social interaction and active lifestyles. Undoubtedly, Hollow Park is more than just a park; it is a testament to Woodbury’s strong sense of community and love for outdoor activities.

Secure Haven

Safety is always a concern for families when considering a move to a small town, and Woodbury Ct ranks high in terms of security. With a low crime rate, residents can feel secure in their community while children play in the beautiful parks or walk to and from school.

The town of Woodbury has an emergency management team standing by 24/7, ensuring that residents are well-protected even in times of crisis. The emergency services in Woodbury are volunteer. Both have community member volunteers that answer any calls of distress.

The Woodbury Volunteer Fire Department was officially recognized on June 7, 1928 and responds to approximately 310 calls for assistance /emergencies a year.

The Woodbury Ambulance Association (WAA) is a professional, volunteer, based ambulance service providing emergency medical services to the town of Woodbury, for over forty years

Affordable Real Estate

In terms of affordability, Woodbury stands out as a budget-friendly place to reside. In comparison to neighboring towns in Fairfield County. Woodbury Ct offers homes at a more accessible price point. For instance, in 2019, the average home price in Woodbury was approximately $355,000, while in nearby Fairfield County, it reached $656,000.

By opting to settle in this charming small town, particularly in Woodbury Ct, you can not only save money but also relish the luxury of spacious houses with ample open areas, if that’s your preference. Woodbury caters to families and presents a diverse range of housing options, from impeccably preserved historic homes to delightful Cape Cod-style houses, ensuring there’s a perfect match for every taste and desire. Immerse yourself in the tranquility and allure of Woodbury, where you can discover the ideal home that fulfills your dreams of comfort and space.

Restaurant Capital

Woodbury is transitioning from the antique capital of the world to a world-class dining destination. All of Litchfield County is renowned for being a fine dining destination and several of the area’s best eateries are located in Woodbury.

New Morning Market, is an independent family-owned natural foods store committed to providing local, organic, and delicious food to its community since 1971. If it’s local and organic-they have it.

For true farm-to-table, visit Carol Peck’s Good News Café. The New York Times called Carol Peck “the Alice Waters of the East Coast. For thirty years she has been offering innovative, farm-fresh food and won numerous national and statewide awards while doing it.

You might also visit the John’s Café a cozy New England bistro with an upstairs lounge & a menu of New American-Mediterranean cuisine.

For the most authentic croissant this side of the Atlantic visit Ovens of France and try some of the finest in pastries, breads and cookies around.

For a classic steakhouse experience, The Market Place Kitchen & Bar is a local favorite, offering hearty portions of prime rib, crab cakes, and baked stuffed shrimp.

Another must-visit spot is the Dottie’s Diner, an iconic 1950s-style diner serving classic comfort foods, such as pancakes, omelets, and milkshakes. Try their award-winning doughnut. If you go early try to get a Jelly.

The Woodbury Brewing Company, located in a renovated historic barn, offers craft beers, casual fare, and a spacious outdoor patio.

On weekends, the popular Woodbury Flea Market brings together a diverse array of vendors offering a variety of items, including antiques in a scenic park setting.

There are three garden shops in town that cater to the needs of gardening enthusiasts. All are local, family-owned shops with a lot of knowledge and a large variety of native and exotic plants. Woodbury Farm Market Garden Center, which offers a wide variety of plants, gardening tools, and accessories.

The second one is The Garden, known for its extensive selection of exotic plants and expert advice on landscaping. Lastly, we have Youngs at Three Rivers, providing personalized service and high-quality plants. Whether you’re a beginner or an experienced gardener, these shops have everything you need to create your dream garden.

Woodbury’s Thriving Arts Scene

With galleries, theaters, and local art events, Woodbury Ct fosters a thriving arts culture that engages both residents and visitors alike. One of the most popular art destinations in town is the Fine Line Art Gallery.

Located in the heart of the historic district, this gallery features works from over 50 local artists who specialize in everything from acrylics and watercolors to photography and sculpture. Whether you’re a seasoned collector or a first-time buyer, the Fine Line Gallery is a must-visit spot to admire some of the most creative and unique artworks in town. 

Created by individuals, the Arts Alliance of Woodbury is an all-volunteer, ‘not-for profit’ nascent organization committed to fostering the arts in Woodbury and surrounding towns. The mission of the Arts Alliance of Woodbury is to promote innovation, creativity, participation and support of the arts.

Members include founders from the Woodbury-Bethlehem Community Music Foundation, Inc [WBCMF]; Community Theatre at Woodbury [CTAW], Hi5netTV’s ‘First Thursdays’, Main Street Ballet, and distinguished sculptors, artists, performing artists, authors, actors and designers and most importantly, the PATRONS of the arts – both large and small.

The Arts Alliance hosts once-a-month “art walks” that showcase individual artists all along the main street in Woodbury.

this event brings together over 30 artists, galleries, and shops in town to display their art and craftworks in a festive street fair setting. Visitors can stroll through the town’s central streets, admire the local art scene, and sample some delicious food and drinks from the town’s restaurants and cafes.

The event also features live music and performance art, as well as art demonstrations and workshops for both kids and adults. It is held on the 3rd Saturday of the month all summer long.

A Town For All Seasons

Whether it’s the vibrant colors of fall, the bloom of spring, or the community gatherings in summer and winter, Woodbury is truly a town for all seasons. Its warm community, rich history, and scenic landscapes make it a sought-after destination for those looking to settle in a place that feels like home.

In Woodbury, the old meets the new, nature meets culture, and every street has a story to tell. It’s not just a place to live; it’s a place to belong.