Located in the scenic Litchfield Hills region of Connecticut, Sherman stands as the northernmost and least populous town in Fairfield County. Though it's the smallest by land area in the county, spanning about 23.4 square miles in the Housatonic Valley at the northern end of Candlewood Lake, this charming rural community has earned the title of "Best Small Town in Connecticut" three times from Connecticut Magazine. Incorporated in October 1802 from the northern portion of New Fairfield and named after Founding Father Roger Sherman from New Haven, the town has a population of approximately 3,527 based on the 2020 census, with projections estimating around 3,641 by 2025. It's a favored weekend getaway for New York City residents, with about a third of its inhabitants being part-time weekenders, drawn to its peaceful, lakeside setting.
Much like the surrounding New England countryside, Sherman's fall
landscape transforms into a breathtaking display of vivid reds, oranges,
and yellows as the leaves change color, making it an ideal spot for
foliage enthusiasts.
Don't miss the Sherman Historic District,
listed on the National Register of Historic Places since 1991, which
showcases well-preserved architecture from the town's early days,
including historic homes, the town hall, school, and former
manufacturing sites—bounded roughly by Old Greenswood Road, Route 37,
Route 39 North, and Sawmill Road. The area around Candlewood Lake,
Connecticut's largest man-made lake, offers stunning waterfront views
and is a highlight for nature lovers.
Other notable sights
include the Connecticut Audubon Society's Deer Pond Farm, a 835-acre
preserve with trails for birdwatching and environmental education, and
the Old Store Gift Shop & Museum, a historic spot dating back
generations that offers a glimpse into local history.
Head to Sherman Town Park at the northernmost point of Candlewood Lake for outdoor recreation, including swimming, picnicking, boating, and fishing on the lake's pristine waters. For wine enthusiasts, visit White Silo Farm & Winery, a family-run operation on a historic farm offering tastings of unique fruit wines like rhubarb and black currant, along with seasonal events and farm-fresh produce. Hiking opportunities abound, with a section of the iconic Appalachian Trail running through the northern part of town, and nearby preserves like Herrick Preserve, Town Meadows, and Wimisink Preserve providing trails for walking and wildlife spotting. Catch a show at the Sherman Playhouse, a community theater hosting plays and performances year-round. Just a short drive away, Squantz Pond State Park in neighboring New Fairfield offers additional activities like hiking, swimming, and canoeing amid forested hills. For families, check out the Sherman Library for events or the Pawling Farmer's Market nearby for local goods.
By Car
The most straightforward way to reach Sherman is by
vehicle, given its rural location. From the east or west, take
Interstate 84 to Danbury, then head north on CT-39 through New Fairfield
to arrive at the town center. If coming from the New York City area,
follow I-684 north, then connect to Routes 22/37 from Brewster for a
direct path. From the north, use Route 7 south or Route 22 south, then
transition to Routes 55/37 to enter Sherman. The drive from NYC
typically takes about 90 minutes, making it an easy escape for urban
dwellers.
By Plane
Several airports serve the region with
varying flight options and drive times to Sherman:
Stewart
International Airport (SWF) in Newburgh, NY (about 70 minutes away):
Offers flights to destinations like Philadelphia, Orlando, Fort
Lauderdale, Atlanta, and Detroit via carriers such as Allegiant and
Frontier.
Tweed New Haven Regional Airport (HVN) in New Haven, CT
(about 90 minutes away): Primarily connects to Philadelphia through
American Airlines.
LaGuardia Airport (LGA) in Queens, NY (about 90
minutes away): Features dozens of domestic and international flights on
major airlines.
Bradley International Airport (BDL) in Windsor Locks,
CT (about 100 minutes away): A hub with extensive worldwide connections
via airlines like Delta, United, and Southwest.
John F. Kennedy
International Airport (JFK) in Queens, NY (about 100 minutes away):
Handles global flights from numerous carriers.
Newark Liberty
International Airport (EWR) in Newark, NJ (about 2 hours away): Another
major international gateway with broad airline options.
Sherman lacks public transportation, so you'll need to rely on driving your own car or walking for shorter distances. The town's rural roads are also suitable for biking, especially for leisurely explorations around the lake or historic areas, but be mindful of hilly terrain and limited shoulders.
For a classic American meal, stop by the American Pie Company, a cozy family-style spot at the junction of Routes 37 and 39, dishing out hearty burgers, crispy fries, homemade pies, and a variety of desserts, plus bakery items and grab-and-go options. Italian cuisine shines at Limoncello Trattoria Napoletana on Route 37 East, specializing in Neapolitan dishes like pasta, pizza, and seafood in a welcoming atmosphere—perfect for holiday parties or catering. Other favorites include Amore for more Italian fare, The Painted Lemon for casual dining, and the Sherman IGA Deli for quick sandwiches and local groceries. For a nearby option, McKinney & Doyle Fine Foods Cafe in Pawling offers upscale comfort food just a short drive away. Don't forget Sacred Ground Coffee Roasters for artisanal coffee and light bites.
Options in Sherman are limited but charming—head to White Silo Farm & Winery for tastings of their farm-produced wines in a scenic garden setting. For pubs and bars, venture nearby to O'Connor's Public House in Pawling for Irish-inspired drinks and pub grub, or The Old Oak Tavern in Gaylordsville for a rustic atmosphere with craft beers and cocktails. The White Horse Country Pub & Restaurant, also close by, serves up drinks alongside brunch and dinner menus seven days a week.
Sherman itself has few lodging options due to its small size, but charming nearby accommodations abound. Consider Candlelight Farms Inn in New Milford, a romantic B&B on a working farm with cozy rooms and scenic views. The Cottages at Kent Road offer quaint, self-contained stays, while the Maple Leaf Motel and Rocky River Inn provide affordable, comfortable motel-style rooms in New Milford. For luxury, the Mayflower Inn & Spa in Washington is an Auberge Resorts Collection property with upscale amenities like farm-to-table dining and spa services, about 20 minutes away. Vacation rentals and Airbnbs are popular for lakeside stays, and larger hotels like Hotel Zero Degrees in Danbury (about 30 minutes south) cater to those seeking more urban conveniences.
Early History and Indigenous Inhabitants
The area that would
become Sherman, Connecticut, was originally inhabited by Native
Americans of Algonquian lineage, specifically the Schaghticoke tribe.
Chief Squantz and his people resided in the region, with accounts
varying on land transactions with European settlers. In 1724, colonists
from Fairfield, Connecticut, received approval from the Connecticut
General Assembly to establish a new township. One narrative suggests
negotiations with Chief Squantz, while another claims he refused to sell
and relocated to the north end of Squantz Pond, where he died in 1725;
his heirs also declined, leading settlers to obtain signatures from
other Native Americans in 1729 who may not have had full authority. On
April 24, 1729, "The Proprietors" purchased a 31,000-acre tract for 65
pounds sterling (about $300), encompassing modern-day New Fairfield and
Sherman; the deed was recorded on May 9, 1729, and is preserved in
Hartford. Originally part of a 1707 land grant to Fairfield settlers,
the area included Quaker Hill and faced boundary disputes, resulting in
the "Oblong" strip being ceded to New York in 1731. By 1736 or 1737, the
"Upper Seven Miles" (future Sherman) was separated from the "Lower Seven
Miles" (New Fairfield). In 1742, the Connecticut General Assembly
established it as a parish with its own church.
Settlement and
the Influence of Roger Sherman
Early colonial settlement focused on
agriculture and small industries. In 1743, Roger Sherman, a young
shoemaker and surveyor from Newton, Massachusetts, moved to the area
(then known as New Dilloway) with his family to join his brother William
near the future Town Hall site. Roger operated a cobbler's shop in the
north end of town, which has since been reconstructed behind the
Northrup House in the town center. He rose to prominence as a Founding
Father, signing all four key U.S. documents: the Continental Association
(1774), Declaration of Independence (as part of the drafting committee
with Jefferson, Adams, Franklin, and Livingston), Articles of
Confederation, and U.S. Constitution (where he proposed the Great
Compromise for bicameral representation). Sherman served in the
Continental Congress, Connecticut's House and Senate, and held public
office for nearly 50 years, longer than any other Founding Father. The
town was named in his honor upon incorporation.
Incorporation and
19th-Century Growth
Sherman was incorporated in October 1802 from the
northern part of New Fairfield, with an initial population of about 150.
Originally called the "Upper Seven Miles," it was renamed for Roger
Sherman. David Northrop served as the first town clerk. Development
centered on the intersection of Routes 37 and 39, featuring a sawmill,
tannery, hat shop, carriage factory, store, church, burial ground,
schoolhouse, and about 15 dwellings by the early 19th century. In 1812,
local men marched to New London to defend the port during the War of
1812. A post office opened in 1818, and stagecoach connections with
regular mail service began in 1820, linking to Poughkeepsie, Pawling,
Quaker Hill, Sherman, and Litchfield.
Economic activities included
agriculture (dairy, sheep, cattle for New York markets) and waterpowered
industries along Sawmill and Greenwood Brooks, such as gristmills, cider
mills, tanneries, and hat manufacturing. In 1829, David Northrop Jr.
operated a general store and built his house (now the Northrop House
Museum). In 1835, Florence and Cyrus Hungerford donated land for the
Congregational Church. "The Playhouse" (Center Church) was built around
1837 for multiple denominations. A sawmill under Albert Barnes operated
in 1839, and by 1845, the Edwards Hat Shop produced 600 hats valued at
$1,500. Tobacco farming started in 1848 and became a major cash crop by
the early 1900s, with leaves dried in barns for cigar wrappers. Access
improved via turnpikes (Sherman-Redding, extended to New Milford in
1820) and a 1840 train route from New Milford to Bridgeport, though no
railroad reached Sherman directly.
The population grew to 948 by the
mid-19th century (984 in 1850) but began declining as youth sought
opportunities elsewhere. During the Revolutionary War (1775-1783),
Captain William Giddings served under General Washington, and in October
1778, Washington's army passed through north Sherman, encamping near a
famous oak in Gaylordsville en route to Boston. The Civil War
(1861-1865) impacted the town, with store ownership changes and economic
shifts. A fire in 1867 destroyed many early town records. Institutions
included early schools like the 1853 District School and Sherman Academy
in the Hawley Store. Telephone service arrived in 1882, road guide
boards in 1883, and the first Town Hall was erected in 1886. The
original Congregational Church burned in 1891 and was rebuilt in 1893.
20th-Century Developments and Preservation
Population declined to
below 600 by 1900, hitting a low of 391 in 1930. A Rural Free Delivery
Route started in 1902. In 1903, Ruth Rogers founded The Delvers literary
club to support library funds. Lake Mauweehoo was created in 1906-1908
by locals and summer residents as a private club. Chris Hansen dammed
for Spring Lake in 1907. The U.S. government closed the post office in
1907 after protests. Fuller's Tavern burned in 1912, and a public
library was established in 1914 with donations from Mrs. Warren Allen
and Jane Mallory Mars. Frank A. Boerum opened the last blacksmith shop
in 1915. The town acquired The Playhouse in 1921 for preservation.
Giddings Garage operated from 1921-1972. A WWI memorial rock was placed
in 1923 for 21 local men. The Sherman Players theater group formed in
1925 to save The Playhouse.
Connecticut Light and Power's
hydroelectric project created Lake Candlewood in 1927-1929, flooding the
Rocky River Valley and Leach Hollow village, relocating graves, and
spurring growth with improved Routes 37 and 39. A consolidated school
opened in 1936, replacing rural ones. Zoning laws began in 1937.
Veterans Field, a WWII memorial, was created in 1947. Population
recovered to 549 by 1950, doubling by 1954, and tripling since WWII by
1970. The Naromi Land Trust formed in 1968 for open space preservation,
creating 30 1,000-acre reservations by the mid-1990s. Wetland
protections in 1973 exempted 11% from development. The Sherman
Historical Society was established in 1975 to preserve artifacts,
buildings like the Old Store Museum & Gift Shop (over 200 years old,
featuring exhibits on general stores and books like Lake Mauweehoo
History), Northrop House Museum, and Roger Sherman Learning Center with
timelines and research tools. Mary Mallory Pattison donated land for
Mallory Town Hall in 1975 (built 1975-1977). New zoning in 1977 (amended
1987) required 2-acre lots. Citizens preserved Ten Mile Hill in
1979-1980 for the Appalachian Trail. The Sherman Historic District,
encompassing the town center with 64 resources (houses, mills, schools)
in styles like Colonial, Federal, and Greek Revival from circa
1740-1937, was added to the National Register of Historic Places on
August 31, 1991.
Modern Era
Population grew to 2,809 in 1990
and 3,827 in 2000. The Historical Society continues programs, including
reenactments (e.g., 2025 50th anniversary "shots heard 'round the
center" with colonial militias), scholarships, exhibits on colonial
taverns, and plans for the U.S. 250th anniversary in 2026 focusing on
Roger Sherman. Sherman maintains its rural character in the scenic
Housatonic Valley at the northern end of Candlewood Lake, with a single
K-8 school and traditional New England village center.
Sherman, Connecticut, a small rural town in northern Fairfield County
with a population of around 3,600, is known for its serene landscapes,
historic charm, and proximity to Candlewood Lake. While it lacks the
dramatic haunted hotspots of larger Connecticut towns like Dudleytown in
Cornwall or the Warrens' famous investigations in nearby areas, Sherman
has a few subtle legends tied to its history, old structures, and the
creation of the lake. These stories often blend local folklore with
whispers of the paranormal, amplified by the town's quiet isolation.
Haunted Legends in Sherman
Sherman's haunted lore is modest and
often tied to its historic buildings and cemeteries, reflecting the
town's 18th-century roots (it was incorporated in 1802 and named after
Founding Father Roger Sherman). Reports are sporadic, typically shared
in paranormal databases, local histories, and online forums, rather than
major investigations. The town doesn't have blockbuster ghost stories
like those in Southington or Burrillville (RI), but eerie sightings and
unexplained phenomena have been noted.
Christ Episcopal Church
(also known as Sherman Congregational Church in some records)
Built
in 1888 on Route 39, this Gothic Revival-style church is one of
Sherman's oldest standing religious sites and a focal point for local
ghost stories. According to paranormal reports, the building is haunted
by apparitions and shadowy figures that appear around the altar, in the
pews, and near the organ. One prominent legend involves the ghost of an
elderly female parishioner, dressed in Victorian-era Sunday clothes, who
is seen sitting quietly in a pew about halfway back during quiet hours
or evening services. Witnesses describe her as peaceful but startling,
vanishing when approached. Other accounts mention fleeting shadows that
dart across the nave, cold spots in the sanctuary, and the faint sound
of hymns or footsteps when the church is empty. These phenomena are
attributed to former congregation members who lingered after death,
possibly due to the church's role as a community hub during epidemics
like the 1918 flu or earlier hardships. No violent or malevolent
activity has been reported, making it more of a "residual haunting" in
paranormal terms. The church remains active for services, but visitors
interested in history can explore its exterior and grounds respectfully.
Leach Hollow Cemetery and Other Old Graveyards
Sherman's cemeteries,
including the historic Leach Hollow Cemetery (also called Leach family
cemetery), carry legends of unrest tied to the town's past. In the early
20th century, as Candlewood Lake was created (see abandoned places
below), graves from Leach Hollow in southern Sherman were supposedly
relocated to higher ground to avoid flooding. However, local folklore
persists that not all bodies were properly moved—rumors of incomplete
exhumations lead to stories of "wandering spirits" or ghostly lights
seen near the original site, now underwater or along the lake's edge.
Some divers and boaters report eerie sensations or unexplained shadows
in the water, linking it to displaced souls. More broadly, Sherman's old
burial grounds (like the Center Cemetery on Route 37) are said to host
"white lady" apparitions, a common Connecticut urban legend where a
spectral woman in white wanders, mourning a lost love or tragic death.
These sightings are rare but mentioned in CT ghost compilations, often
during foggy nights or full moons. No formal investigations have
confirmed activity, but the legends add to the town's atmospheric vibe.
General Folklore and Nearby Influences
Sherman itself isn't a hotbed
for legends, but its proximity to haunted sites in neighboring towns
bleeds over. For instance, tales of the "Melon Heads" (feral, deformed
children from a cruel institution) from nearby Kent or New Milford
sometimes extend to Sherman's wooded areas. Additionally, the town's
quiet roads and farms inspire stories of phantom hitchhikers or orbs
seen in fields, possibly linked to Revolutionary War-era deaths (Sherman
was part of New Fairfield during the war). These are more anecdotal,
shared on Reddit threads or CT urban legend sites, without substantiated
evidence.
Overall, Sherman's hauntings are subtle and benevolent,
fitting its low-key reputation. Paranormal enthusiasts might find the
town underwhelming compared to flashier spots, but it's ideal for those
seeking atmospheric, understated eerie experiences.
Sherman's "abandoned" sites are largely tied to natural and
industrial changes rather than dramatic ruins. The creation of
Candlewood Lake in the 1920s submerged parts of the town, creating a
unique underwater "ghost town" legacy. Other spots feel abandoned due to
disuse or decay.
Jerusalem Village (Underwater Ruins in
Candlewood Lake)
One of Sherman's most intriguing abandoned places is
the submerged remnants of Jerusalem, a 19th-century farming and milling
community in the Rocky River valley. Bordering Sherman, New Fairfield,
and other towns, Jerusalem included homes, mills, schools, and farmlands
housing about 35 families. In 1926–1928, the Connecticut Light and Power
Company dammed the area to create Candlewood Lake (New England's largest
man-made lake) for hydroelectric power, flooding the village. Structures
like stone foundations, roads, tools, and even a rumored graveyard were
left below the surface. Divers today explore these eerie ruins at depths
of 20–60 feet, finding moss-covered walls, rusted machinery, and
artifacts like old bottles—creating a time-capsule effect. Legends add a
haunted layer: some claim the flooding disturbed spirits, leading to
reports of underwater "currents" that feel like hands pulling or ghostly
figures in the murk. Access is via boat or scuba (with permits), but low
water levels occasionally reveal edges. This isn't a traditional ghost
town but a literal drowned one, symbolizing progress's cost.
Leach Family Cemetery Site (Relocated for Candlewood Lake)
Tied to
the lake's creation, the Leach family cemetery in southern Sherman was
disinterred in 1918–1928 to prevent flooding. Historical documents note
the need to move remains "beyond high-water mark," but rumors persist
that some graves were overlooked, contributing to lake hauntings. The
original site is now submerged or overgrown, feeling abandoned and
eerie. No visible ruins remain above water, but it's a poignant reminder
of displacement—visitors can hike nearby trails in Squantz Pond State
Park for views of the lake and reflections on the lost history.
Other Semi-Abandoned or Historic Sites
Old Farms and Barns: Sherman's
rural character includes derelict barns and farmhouses along routes like
37 or 39, some dating to the 1800s. These aren't officially abandoned
but often appear so, with overgrown fields evoking a "time-forgotten"
feel. Local Instagram posts describe them as having a "ghostly Main
Street" vibe.
Nearby Hearthstone Castle (in Danbury, ~10 miles
south): While not in Sherman, this 1897 ruined castle—abandoned since
the 1980s—looms large in regional lore. Its graffiti-covered stone walls
and towers are said to host whispers, cold spots, and shadowy figures.
Owned by the city but closed to the public, it's a short drive and often
lumped with Sherman's eerie spots due to proximity.