Southbury, Connecticut

Southbury is a charming town nestled in the scenic Litchfield Hills region of northwestern Connecticut, specifically in western New Haven County. Covering about 39 square miles, it offers a blend of rural beauty with rolling hills, rivers like the Pomperaug and Housatonic, and a vibrant community atmosphere that appeals to both residents and visitors. Known for its agricultural heritage and natural landscapes, the town provides a peaceful escape while being conveniently located near larger cities.

 

See

One of the standout attractions in Southbury is the Shepaug Dam, a hydroelectric facility operated by FirstLight Energy that spans the Shepaug River where it meets Lake Lillinonah on the Housatonic. It's particularly famous for its bald eagle observation area, which opens from the third weekend in December through early March, allowing visitors to spot wintering eagles in their natural habitat—often soaring or perching near the water. In warmer months, from Memorial Day to Labor Day, the surrounding recreational area transforms into a spot for hiking along the half-mile interpretive trail, picnicking, and fishing along the lakeshore. This site has been a popular eagle-watching destination for over 30 years, drawing nature enthusiasts who can bundle up for guided views during the colder season.

 

Do

For a relaxing escape, head to the Adam Broderick Salon & Spa at 730 Main St S (phone: +1 203-267-4334), a top-rated destination in Southbury for unwinding and self-care. Open Monday through Wednesday from 8:30 AM to 9 PM, Thursday until 10 PM, Saturday from 8 AM to 6 PM, and Sunday from 8 AM to 5 PM, this full-service spot goes beyond basics with a wide array of offerings including therapeutic full-body massages, advanced facial and skin treatments, and even vitamin therapy or exfoliating body polishes for a luxurious spa experience. Hair services are equally comprehensive, featuring cuts, coloring, retexturizing, extensions, and specialized treatments, all in a welcoming environment with amenities like steam showers, lockers, and a cozy relaxation room. With locations in both Southbury and nearby Ridgefield, it's a favorite for locals seeking professional, results-driven pampering.

 

Get In

Southbury is easily accessible by car via Interstate 84, which runs through the area and connects to major highways. For those flying in, the nearest major airports are Bradley International (BDL) in Hartford or Tweed New Haven (HVN), with ground transportation options like Connecticut Limo or AAA Cab Service available for transfers. Public transit includes CT Transit bus routes serving the region, and Metro-North Railroad stops in nearby towns for rail connections. Taxis and rideshares like Uber are also readily available for door-to-door service.

 

Get Around

Navigating Southbury is straightforward with various car services and limo options, many of which can be arranged from local hotels such as the Heritage Hotel or what was formerly the Crowne Plaza (now possibly rebranded). Popular providers include Rosa Ride, Village Driver Service, Gateway Limousine, and Absolute Transportation, offering reliable chauffeured rides for town exploration or airport shuttles. For a more active approach, biking is a favored way to get around during milder seasons, thanks to the town's scenic roads and trails that make cycling enjoyable and eco-friendly.

 

Buy

Southbury boasts a selection of unique shops perfect for browsing and picking up souvenirs or gifts.

Gayle O'Neill Fine Jewelry, 775 Main St S (phone: +1 203-264-0600). Open Monday to Saturday from 10 AM to 6 PM and Sunday from noon to 5 PM. This family-owned boutique specializes in a mix of antique, contemporary, and estate jewelry for men and women, including diamonds, colored gemstones, and custom pieces at affordable prices. The inviting atmosphere is complemented by services like jewelry repairs, gold and platinum buying, making it a go-to for both everyday accessories and special occasion finds.
Marie's Country Furnishings, formerly at 330 Main St S (phone: +1 203-264-0488). Note: As of 2025, this beloved spot has transitioned into Marie's Movers, shifting focus from retail home decor to professional moving services across Connecticut and nationwide. Originally known for its charming collection of craft collectibles, antique furniture, and distinctive New England-style home accents, it was a quaint stop for unique decor items. For similar shopping, consider exploring other local antique spots in the area.
Newbury Place, 41 Oak Tree Rd (phone: +1 203-264-7333). Open Monday to Wednesday from 9:30 AM to 5:30 PM, Thursday until 7 PM, Friday and Saturday from 9:30 AM to 5:30 PM, and Sunday from 11 AM to 4 PM. Housed in a historic 150-year-old mill, this popular gift shop offers an eclectic assortment of clothing, jewelry, purses, accessories, and thoughtful presents that delight both locals and tourists alike. It's been a community staple for years, serving multiple generations with its curated, one-of-a-kind selections.
Class Cycles, formerly at 77 Main St N (phone: +1 203-264-4708). Note: As of 2025, this shop appears to have closed its doors. It previously offered a range of new and used bicycles, along with expert repairs and maintenance, supported by a friendly and experienced staff knowledgeable in everything from kids' bikes to high-end triathlon models. For cycling needs today, check out nearby alternatives or online retailers specializing in bikes.

 

Eat

Heritage Deli & Cafe, 466 Heritage Rd, ☏ +1 203 264-4322. M-F 6AM-6PM. Established in 2004, this beloved spot has been delighting sandwich enthusiasts in Southbury for over two decades with its fresh breakfast and lunch selections. The menu features an array of hot and cold sandwiches, including standout options like the Wicked Chicken, Mesquite Smoked Turkey, house-made roast beef, and turkey wraps, with the flexibility to customize your own creation. Affordable prices, friendly service, and specials like the early bird breakfast sandwich for just $1 make it a go-to for locals and visitors alike, complete with indoor/outdoor seating near the Southbury Green and convenient mobile ordering via ChowNow.
Denmo's Snack & Dairy Bar, 340 Main St S, ☏ +1 203 264-4626. Spring and summer: 11AM-10PM daily (hours adjust seasonally). Right in the heart of Southbury, this classic drive-in embodies traditional American roadside dining, famous for its hot dogs and affordable eats. The varied menu includes favorites like foot-long charred hot dogs, hamburgers, onion rings, fried whole belly clams, clam strips, and chocolate milkshakes, plus ice cream treats for dessert. With pet-friendly outdoor picnic tables and a casual eat-in-the-rough vibe, it's a local gem for quick, satisfying meals, though some note occasional inconsistencies in portions like clams.
Leo's Restaurant, 7 Poverty Rd, ☏ +1 203 264-9190. M-F 8AM-8:30PM, Sa-Su 8AM-3PM. This intimate, family-run Italian eatery boasts scenic balcony views, budget-friendly pricing, and consistently warm staff. Specializing in homemade foods with creative twists, it's renowned for breakfast staples like challah French toast, fluffy waffles, and fresh orange juice, earning "Best Breakfast" accolades from Connecticut Magazine. The menu extends to lunch and dinner with unique concoctions, generous portions, and options like the Bocco Chicken or Steak Bocco, all in a clean, family-oriented atmosphere.
DiPalma's Pizza, Union Square, ☏ +1 203 264-3555. Tu-Sa 11AM-9:30PM, Su noon-9PM. Standing out among Southbury's pizza options, DiPalma's delivers exceptional New York-style pies hailed as the town's best for their crispy crusts and flavorful toppings. Beyond pizza, the menu includes grinders, pastas, antipasti, and specialties like Margherita pizza, chicken Parmigiana, and chicken tenders, with terrific sauces and generous servings in a warm, inviting setting. It's a local favorite for both dine-in and takeout, though some note the absence of veal dishes and occasional skimpy toppings on grinders.

 

Drink

Rathskeller Bar & Grill, 88 Main St S, ☏ +1 203 264-0186. M-Sa 11:30AM-10PM, Su noon-9PM. Positioned on the corner of Main Street South, this intimate bar and grill fosters a friendly vibe with reasonably priced drinks, making it a favored evening hangout. The menu highlights American classics like cherry chicken, pecan chicken, corned beef Reuben, and Rathskeller burgers, alongside gluten-free choices and a curated wine list. Under new ownership, it offers improved food quality, attentive service, and a clean space ideal for casual dining or private parties.
Fairways Tavern & Terrace, 137 E Hill Rd, ☏ +1 203 405-6270. Tu-Su noon-9PM. Housed within the Southbury Country Club, this full-service restaurant and bar provides lunch and dinner in a relaxed setting. It blends elevated bar bites with classic entrees using seasonal fresh ingredients, featuring a chic cocktail bar with top-shelf liquors, 10 beers on tap, an extensive cocktail menu, and all-day brunch on Sundays. The pub-style cuisine with a New England twist makes it a great spot for gatherings.
The Lodge Bar & Grill, 1455 Southford Rd, ☏ +1 203 267-6974. Su-Th 11:30AM-11PM, F-Sa 11:30AM-midnight. On the border of Southbury and Southford, this venue delivers lunch and dinner across inviting spaces like a dining room, outdoor patio, pub, and lounge. The menu offers hearty fare such as Angus burgers, wings, salads, Philly cheese steaks, and house-made desserts, with daily specials like Wing Mondays and Taco Tuesdays. Entertainment includes a free pool table, TouchTunes, Thursday trivia, and a welcoming, Cheers-like atmosphere with locally sourced rotating draft beers.

 

Sleep

Wyndham Southbury (formerly Crowne Plaza Hotel), 1284 Strongtown Rd (off Exit 16 on I-84), ☏ +1 203 598-7600. Check-in: 3PM, check-out: noon. This upscale hotel provides daily breakfast specials at its on-site Arrowhead restaurant, serving American cuisine for all meals. Amenities feature non-smoking rooms with free high-speed WiFi, ergonomic workspaces, plush bedding, spa-style bath products, an indoor pool, sauna, modern gym, business center, and a complimentary shuttle within a five-mile radius. Its rural yet convenient location near attractions like Quassy Amusement Park makes it ideal for business or leisure.
The Heritage Hotel, 522 Heritage Rd, ☏ +1 203 264-8200. Enveloped by scenic hillsides, this resort-style hotel offers a broad spectrum of leisure and entertainment options, from spa services and jacuzzi relaxation to Zumba classes and golf memberships. Guests enjoy indoor and outdoor pools, a fitness center, tennis courts, hiking trails, basketball, an arcade, and pet-friendly accommodations in spacious rooms with free WiFi and premium amenities. It's a top choice for conferences, weddings, or getaways, with recent renovations enhancing its rustic charm and modern comforts.

 

History

Pre-Colonial and Early Settlement Period
The area now known as Southbury, Connecticut, was originally inhabited by Native American tribes, including the Pootatuck Indians, a subgroup of the Paugussetts, who lived along the Pomperaug and Housatonic Rivers. These indigenous peoples did not have a concept of private land ownership, and their interactions with early European settlers were generally peaceful, involving land sales in exchange for goods like clothing, tools, and firearms. The recorded European history begins in 1673, when religious dissidents from Stratford, Connecticut Colony, dissatisfied with church governance, negotiated the purchase of land called the "Pomperaug Plantation" from the Pootatuck Indians. This transaction, formalized on April 26, 1673, involved fifteen families led by Reverend Zechariah Walker, who rafted up the Housatonic River to establish one of the farthest inland settlements from the coast at the time. The settlers camped under a large white oak tree in the White Oak section (near present-day Settlers Park) on their second night, marking the first European encampment in what would become Southbury.
The settlement was initially part of "Ancient Woodbury," renamed in 1674 to mean "a dwelling in the woods." Additional land acquisitions followed, including the Kettletown purchase in 1679 (reconfirmed in 1706 after an earlier rumored exchange for a copper kettle), the Shepaug Purchase in 1686, and the Quassapaug Purchase in 1687. The Pootatuck retained hunting rights and a reservation along the Housatonic River (now partially submerged under Lake Zoar). Life in the early settlement was church-centered, with Fundamental Orders establishing land division, taxation (including ministerial support), and education provisions—ensuring children were taught to read and write, a progressive stance for the era. Prominent families like the Hinmans, Stiles, Curtisses, and Mitchells arrived and have remained influential for generations.

Colonial Development and the Revolutionary War
For over a century, the region remained agrarian, with homes built closely for security and basic infrastructure like grist mills. In 1731, the southern part of Woodbury formed the Second Ecclesiastical Society, named Southbury, and South Britain became an independent society in 1766. Education was prioritized early, with schools established in districts like White Oak (using the Congregational church from 1770), Bullet Hill (built in the 1760s), and others including Southford, Kettletown, and Transylvania. The Bullet Hill School, constructed in 1762, is the oldest public building in Southbury and served continuously until 1941, making it one of the longest-operating schools in the U.S.; it now hosts living history programs for students.
During the Revolutionary War, Southbury (still part of Woodbury) played a supportive role as a key agricultural supplier, providing food, supplies, and militia volunteers to General Washington's army. Local resident Shadrack Osborne operated a military commissary on Main Street North, issuing provisions to troops. After the British capture of Danbury in 1777, he hid hundreds of pork barrels in a nearby hollow, now called Pork Hollow. In 1781, French General Comte de Rochambeau and his troops marched through Southbury, camping in the White Oak section en route to Yorktown; this event was commemorated in 2006 with parades and reenactments as part of the 225th anniversary of the Washington-Rochambeau Revolutionary Route. The Bullet Hill area was used for firing practice, and the schoolhouse melted bullets for the Continental Army.

Incorporation and 19th-Century Growth
Southbury was incorporated as an independent town on May 10, 1787, by the Connecticut General Assembly, encompassing the Southbury and South Britain societies plus parts of Oxford. The first town meeting occurred on June 20, 1787, moderated by Edward Hinman. In 1798, a portion of Kettletown was ceded to Oxford. Throughout the 1800s, Southbury remained primarily agricultural, but abundant water power from rivers and streams spurred industrial development, especially in villages like South Britain (the main industrial hub) and Southford. Industries included tanneries, clothiers, grist mills, saw mills, cider mills, forges, and factories producing hats, buttons, brads, shears, knives, silver spoons, thimbles, hoop skirts, bustles, and even satinet fabric for Union Army uniforms during the Civil War. By the mid-1800s, the town boasted up to 60 small factories and shops, though many declined as larger urban centers like Waterbury offered more efficient production. The New York & New England Railroad line, built in the 19th century, connected Southbury to broader markets, facilitating trade and travel. Taverns, shoe-making enterprises, and mills for paper and lumber also thrived, while South Britain specialized in carpet and hat-making.
As the nation's centennial approached in 1876, descendants of founding families migrated westward, replaced by Eastern European immigrants who revitalized agriculture amid increasing diversity. The 1873 Old Town Hall now serves as a museum operated by the Southbury Historical Society, housing archives and exhibits on local history.

Early 20th Century and the Nazi Camp Incident
In the early 20th century, Southbury's rural charm attracted attention, notably through resident Wallace Nutting's 1923 book Connecticut Beautiful, which featured photographs of the town and South Britain as part of the Colonial Revival movement. Advancements like hydroelectric dams, automobiles, and improved roads drew urban dwellers for recreation and country living. The town transitioned from factories (many closed in the 1920s) to a mix of old families, immigrants, and newcomers, including professionals and tourists.
A pivotal event occurred in 1937 when the pro-Nazi German-American Bund attempted to establish a training camp in Southbury. The Bund, led by Fritz Kuhn and claiming up to 200,000 members (though likely closer to 15,000 active), operated camps nationwide modeled after Hitler Youth programs, promoting German heritage, militarism, and anti-Semitic ideology amid U.S. isolationism and rising hate groups. On October 1, 1937, Bund member Wolfgang Jung purchased 178 acres in the Kettletown district for Camp General von Steuben, intended to serve Nazis in the Bronx, Westchester, and Connecticut, with facilities for 1,100 people, including a youth hostel and swimming pool. Residents discovered the plans via newspaper reports, sparking outrage in the community of about 1,200.
Local leaders, including First Selectman Ed Core, contacted the FBI and state police, learning that zoning could block the camp. Pastors Reverend M.E.N. Lindsay and Reverend Felix Manley preached anti-Nazi sermons, with Lindsay's calling anti-Semitism "anti-Christ" and "anti-American," gaining national attention. On December 5, 1937, two Bundists were arrested for violating blue laws by working on the Sabbath. A town meeting on December 14, 1937, at the South Britain Congregational Church passed zoning restrictions limiting Kettletown to farming and residential use, with a $250 fine for violations, passing 142-91 despite constitutionality concerns. The Bund dropped plans, sold the land, and threatened another site but never returned to Connecticut. Southbury's stand made national headlines, earning "town of the year" honors in 1938 and serving as a model of community resistance; the story was revived in the 2012 documentary Home of the Brave and exhibits at the U.S. Holocaust Memorial Museum.

Mid-20th Century to Present
Post-World War II, Southbury experienced rapid development. In 1940, the state built a large training school for adults needing residential care. In 1955, Connecticut Light and Power constructed two dams on the Housatonic River. The 1967 establishment of Heritage Village, one of the Northeast's first retirement communities, marked a shift toward residential and commuter living. The town attracted notable residents like comedian Victor Borge, entertainer Ed Sullivan, actors Barbara Hershey, Polly Bergen, and Rosalind Russell, and radio personality Tony Marvin.
Today, Southbury preserves its history through sites like the Southbury Historic District No. 1, which spans Main Street North from Heritage Road to the Woodbury town line and includes architecturally significant buildings from the 18th and 19th centuries. The Southbury Historical Society maintains collections, including property records and evaluations of over 100 historic sites. With a population of around 18,567, the town balances rural charm, stone walls, and farms with modern commuting via major roadways. Initiatives like the Historical Tree Restoration Committee protect natural heritage, and Southbury was designated a Preserve America Community in 2009. Its seal proclaims it "Unica Unica" (Unique Unique), reflecting a distinctive community shaped by centuries of settlement, resistance, and adaptation.
One iconic historic structure is the Nathan Curtiss Tavern, a preserved example of colonial architecture in the town center.

 

Haunted legends and abandoned places

Southbury, a quiet town in western Connecticut, harbors a rich tapestry of eerie folklore and supernatural tales, often intertwined with its rural landscapes and historical sites. Many of these legends draw from colonial-era isolation, mysterious disappearances, and rumored inhuman entities lurking in the woods. While some stories have evolved into urban myths amplified by media and online forums, they continue to attract ghost hunters and thrill-seekers. Below, I'll delve into the most prominent haunted legends associated with the area.

The Melon Heads: Cannibalistic Mutants of the Woods
One of Southbury's most infamous legends revolves around the "Melon Heads," a group of deformed, large-headed humanoids said to inhabit the dense forests surrounding the town. These beings are described as escaped mental patients from nearby asylums (such as those in Newtown) or descendants of an inbred colonial family cursed by isolation and hardship. According to variations of the tale, they survived in the wilderness by resorting to cannibalism, ambushing unsuspecting travelers or hikers for food. Sightings often depict them as hunched figures with oversized, melon-like heads, pale skin, and feral behaviors—such as drinking from reservoirs, breathing heavily behind children in the woods, or making direct eye contact with grotesque faces.
The legend suggests they reproduce sporadically, perhaps intermingling with other escaped individuals from 1970s institutions, extending their myth to neighboring towns like Shelton, Milford, Trumbull, Monroe, Seymour, Weston, and Oxford. Witnesses claim encounters where the Melon Heads place dead animals on roads to cause accidents or swarm vehicles at night. This folklore ties into broader Connecticut hauntings, portraying the woods as a domain of the outcast and monstrous. While no concrete evidence exists, the story persists through oral traditions and has been featured in local media as a staple of southern Connecticut's ghostly lore.

Jeremy Swamp Road: The Road of Disappearances and Phantoms
Jeremy Swamp Road stands out as Southbury's most notorious haunted site, often ranked among the top haunted roads in the United States—earning the dubious honor of "most haunted" by Travel & Leisure in 2023 due to its chilling history of vanishings and spectral encounters. This winding, dimly lit rural path is steeped in tales of inexplicable disappearances dating back decades. Drivers report their vehicles suddenly stalling or breaking down, only to vanish without a trace before help arrives. Notable cases include hikers, motorists seeking aid, and even an entire scout troop that allegedly disappeared en masse, never to be found.
The road's infamy is amplified by associations with the Melon Heads, who are said to lurk in the surrounding woods, ambushing stranded victims or using tactics like placing deer carcasses to force stops. Other accounts describe a ghostly woman—believed to be a hitchhiker killed in a hit-and-run—appearing along the roadside, only to vanish when approached. In more esoteric interpretations, the road functions as a "crossroads" or ley line for souls, a liminal space where the veil between worlds thins. One detailed encounter recounts a phantom entity, captured in a nighttime photo, acting as a guardian of this pathway. This being describes the road as a "road of light" for departing souls seeking respite before reincarnation, but warns of abductions by interdimensional entities during full moons. Those not aligned with the "light path" are advised to steer clear, as the area welcomes sanctuary only for certain spirits while posing dangers to the living.
Historical context links these stories to the road's remote location and poor maintenance, which may have contributed to real accidents and missing persons reports over the years. Modern explorers note an oppressive atmosphere, with reports of orbs, strange sounds, and a sense of being watched, making it a hotspot for paranormal investigations.

Other Ghostly Tales and Urban Legends
Southbury's haunted reputation extends to lesser-known stories, such as apparitions at the former Oak Tree Inn (also called the Old Southbury Inn). This historic building, undergoing renovations in recent years, is rumored to host residual hauntings from its past as a colonial-era tavern. Guests and workers have reported unexplained noises, cold spots, and shadowy figures, though specifics are sparse and often tied to its age and history of ownership changes. Broader Connecticut folklore, including cursed villages and haunted islands, occasionally references Southbury's woodlands as extensions of these eerie narratives, blending with tales from nearby Trumbull and Shelton.

 

Abandoned Places in Southbury, Connecticut

Southbury's abandoned sites often overlap with its haunted legends, creating an atmosphere of decay and mystery. These locations, remnants of institutional and residential history, evoke a sense of forgotten lives and potential unrest. Many are off-limits, with trespassing discouraged due to safety and legal concerns, but they remain subjects of urban exploration and drone footage.

Southbury Training School: A Sprawling Institutional Relic
The Southbury Training School, established in the mid-20th century on a vast 1,600-acre campus, was designed as a residential facility for individuals with intellectual and developmental disabilities. At its peak, it housed thousands of residents in a self-contained community with its own utilities, including independent water and electricity systems. However, admissions ceased in 1986 amid shifting policies toward community-based care, leading to a drastic population decline—by the 2010s, only around 300 residents remained, with much of the campus falling into disuse.
The abandonment is partial: while core operations continue on a smaller scale, vast sections, including administrative buildings, dormitories, and farm structures, stand empty and deteriorating. Old farm trucks and equipment rust in overgrown fields, evoking a time when the school functioned as a working farm for resident therapy. The site's eerie qualities stem from its isolation, with hidden graveyards—possibly containing unmarked graves of former residents—that receive no visitors, fueling speculation about lingering spirits. Drone explorations reveal crumbling infrastructure shrouded in trees, with an unsettling silence broken only by wind through broken windows. Though not explicitly haunted in records, the school's history of institutionalization and potential mistreatment has led to rumors of residual energy, apparitions of former residents, and a pervasive feeling of sadness or watchfulness.

The Abandoned Staff Neighborhood: A Ghost Town of Cottages
Adjacent to the Training School is an entire abandoned residential neighborhood, originally built as housing for staff and their families. This development features dozens of mid-century cottages, complete with paved roads, fire hydrants, and pathways—all eerily maintained for years after evacuation, with lawns mowed and utilities intact despite no occupants. The homes contain identical, outdated furniture, now covered in dust and leaves, giving the area a staged, movie-set quality that's both preserved and neglected.
The abandonment occurred gradually after 1986, as staff reductions followed the school's downsizing. By the late 2010s, the neighborhood had a post-apocalyptic vibe, likened to a "Twilight Zone" episode, with no signs of life for miles. Rumors of demolition circulated around 2018, but the site's status remains unclear, with some structures showing increased decay in recent explorations. Spooky elements include its hidden location at the end of a blocked road, the unnatural quietude, and connections to the Training School's graveyard, sparking theories of hauntings by displaced souls or institutional echoes. Videos from urban explorers highlight creaking doors, overgrown yards, and a nearby spooky cemetery, amplifying its creepy allure.

Additional Abandoned Spots
Scattered around Southbury are smaller ruins, such as isolated abandoned houses along routes like Route 10 (though more prominent in nearby Cheshire) and derelict farm buildings on the Training School grounds. These sites contribute to the town's overall aura of abandonment, often explored in YouTube videos showing boarded-up windows, vandalized interiors, and nature reclaiming the land. While not as documented, they blend into the larger narrative of Southbury's forgotten corners, where history and legend intersect.