Plucked from a classic New England postcard, Middlebury is a small, rural town in New Haven County in the western part of Connecticut. While big city amenities in New Haven are only a short drive away, this quaint town of 7,500 is beloved for its scenic beauty, high-ranking school system and higher education opportunities. Surrounded by lush forests, state parks, rolling hills and lakes, and with nearly 2,000 acres of conserved land. This, coupled with its education system has built Middlebury into a destination for families and outdoor enthusiasts to settle. "It's where small-town living meets urban accessibility," says Brian Shaban, local resident and Public Relations Chairman of the Middlebury Town Committee.
Middlebury has maintained its tight-knit community and managed to fend off the overdeveloped urban sprawl of many of its Connecticut neighbors. "Everyone knows each other and helps each other out," Shaban says. "Almost all businesses are locally owned, and people here strive to keep it a small town. That's part of its charm, and they don't want big box stores, chains and massive developments coming in and changing that." Despite that, it's no ghost town. Within its 18.5 square miles, Middlebury has seven distinct business districts. The town’s largest industries are healthcare, hospitality and education. Its largest employers are Timex Group, Quassy Amusement Park, Waterbury Hospital and Danbury Hospital. Its proximity to major highways, two airports and other major transportation hubs, along with its lower cost of real estate and taxes compared to its New Haven and Hartford neighbors, has made it a desirable destination for businesses to plant roots.
A town surrounded by forests
While there are only around six parks in Middlebury, residents are surrounded by opportunities to get outdoors. The town green is a favorite for exercising, and Meadowview Park is a popular spot for fishing, strolling nature trails and playing basketball.
However, outdoor enthusiasts love that Middlebury is in the middle of several state forests, including Naugatuck State Forest, Mattatuck State Forest and Paugussett State Forest. At the densely wooded 5,000-acre Naugatuck State Forest 7 miles south, residents can go fishing, hiking, mountain biking, hunting, camping and skiing in the winter. The Larkin State Bridle Trail is a popular trek here, and the forest is home to scenic waterfalls and some of the best birdwatching in Connecticut. The 4,500-acre Mattatuck State Forest, just 9 miles north, offers miles of rugged trails with scenic overlooks, including the 36-mile Mattatuck Trail, a hiker favorite, views of the Naugatuck River and diverse wildlife habitats. About 14 miles south of town is Paugussett State Forest, a 1,200-acre nature sanctuary with ponds, towering hardwood forests and well-maintained trails. Besides hiking, it’s a popular spot for fishing, kayaking, camping and hunting.
Residents don’t need to trek out of town to get outdoors. Middlebury's most popular outdoor spot is the 296-acre Quassapaug Lake, boasting a town-owned beach and a prime spot for boating, swimming, picnicking and skiing in the winter. And cyclists frequent the Middlebury Greenway, a paved 7-mile trail that runs through New Haven County.
Mom and pops and America’s oldest amusement park
A quintessential New England small town, most events and happenings are centered around Middlebury Green. Most businesses are locally owned, and many have had roots in town for decades. A family-owned business, Willie’s Wood Smoked BBQ has served the community for nearly 30 years with pulled pork sandwiches, fried chicken and chicken wings. The restaurant’s BBQ was voted in the top 10 in the U.S. by Roadfood.com. The Local Gourmet is the go-to spot for sandwiches, and for an upscale Italian meal and fine cocktail, Vyne Restaurant is a favorite in town. And Pies & Pub has been a staple since 2011. The laid-back joint serves up pizza and a wide variety of craft beer.
While there are no art theaters directly in Middlebury, the ornate Palace Theater is in neighboring Waterbury, only a 5-mile drive. The Renaissance Revival-style theater has entertained crowds since 1921 with local and traveling productions, including Broadway musicals, concerts and comedy.
Middlebury’s biggest entertainment draw is Quassy Amusement Park, one of the nation's oldest amusement parks and one of only 11 trolley parks still operating in the country. Surrounded by Lake Quassapaug, the park offers 20 rides, a waterpark and year-round from the spring to the fall. The park also has the oldest building in the town, a 1910 structure once home to a dance pavilion that now houses Redemption Arcade.
Four Corners Grocery Store is the town's only market, and most shopping is done at Village Square. However, larger shopping outlets are nearby, with Naugatuck Valley Shopping Center, a 9-mile drive from the city center. Its biggest event is “Celebrate Middlebury,” a festival held at Shepardson Community Center to support local businesses, restaurants and organizations.
Cape Cods, historic homes and lakeside retreats
Niche ranked Middlebury the 18th-best place to retire in Connecticut, but its neighborhoods offer more than quiet lakeside retreats. The housing landscape is filled with classic New England homes, historic colonials dating back to the 1700s, starter homes and larger, two-story homes for larger families. In February 2024, the median sale price for a home was $648,500, up 40% from the year prior, and houses stay on the market for 44 days on average.
Many homes come with antique barns, garden areas and lots on multiple acres. Cottages, Cape Cods and other properties near the lake tend to be a little higher but come with more privacy and amenities like boathouses and docks.
Residents in Middlebury Center are surrounded by amenities. The busy area is within walking distance of six restaurants, a grocery store and shopping. The most coveted area, Middlebury Green, is the historic center of town, offers antique colonials and Victorians and is listed as a historic district on the National Register. The neighborhood is home to churches, the Westover School, the town hall, a community center and a library.
Top-notch educational opportunities
Middlebury is served by the Pomperaug Regional School District No. 15, which caters to 3,500 students. Earning an A-plus on Niche, it’s the sixth-best district in the county. State-of-the-art educational facilities are open to the public. The town is also home to Westover, an independent college prep day boarding school for girls in grades nine through 12. Open since 1909, the private school earned an A-plus on Niche and is ranked the fourth-best all-girls high school in the state. College-bound students wanting to stay close to home can attend Naugatuck Valley Community College, the fifth-best community college in Connecticut. Yale University and the University of New Haven are both 23 miles from the city center.
Central to it all
Interstates 8 and 84, State Routes 63 and 64, including New Haven, a 23-mile drive, and Hartford, 35 miles away. Middlebury Greenway is there for cyclists to get from Route 63 to Route 64. The closest airport is the Tweed New Haven Airport, 30 miles away, and the closest international airport is in Windsor Locks, a 50-mile drive. CTtransit, the largest bus service in Connecticut, provides several routes for residents.
Community approach to crime
According to the Middlebury Police Department, violent crimes have been at a record low since 2017, when only 5 were reported. Property crimes are slightly higher but still significantly slower compared to the rest of the state. In 2022, there were 46 property crimes reported in the town. To keep crime down and keep the community engaged, the department hosts annual toy drives and an annual clambake for the town put on the Middlebury Police Social Club to fund its community outreach programs.
Staying a small town for now
In the summer of 2023, Timex Group sold its Middlebury headquarters for $75 million to Southford Park, a development group looking to turn it into a food distribution center. The planned property totals 7000,000 square feet, and while the town’s Conservation Commission approved permits, many town residents have been vocal in opposition to the center. In January 2024, town residents filed a lawsuit to protest approvals made by the conservation and zoning commissions. "The distribution complex is still tied up in court right now, but it's definitely something many of the residents in town do not want," Shaban says.
And in February 2024, the Middlebury Land Trust put forth a proposal for the town’s first dog park near the back of the Nichols Road Preserve.
Shaylene is a licensed Realtor in New York and Connecticut and former owner/partner of her family-owned and operated real estate company Neumann Real Estate, locate in Ridgefield and New Fairfield, CT. Neumann Real Estate joined forces with Houlihan Lawrence on March 2, 2022. This merger combines the power of the number one brokerage in Westchester and Greenwich, providing us with access to the Houlihan Lawrence marketing engine and 1,450+ network of agents.
Shaylene started her real estate career in 1991 and has been active in all aspects of running a real estate company from managing the finances for 30+ years, heading up the relocation department, as well as starting up the IT services for Neumann Real Estate before she went into sales in 2004. Shaylene has been an active Realtor for 18+ years representing both buyers and sellers in all aspects of the real estate transaction. As a horse enthusiast, and a horse owner, Shaylene brings a unique knowledge of the real estate market to prospective buyers and sellers of equestrian properties. She is committed to providing her clients with unparalleled customer service, she has excellent communication and negotiation skills when it comes to putting a deal together and she has intimate knowledge of the local communities in New York and Connecticut.
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