7 Oldest Founded Small Towns to Visit in Connecticut

Norman Rockwell wrote that New England was home to a “people with great strength and unshakable pride.” No more is that true than in the state of Connecticut. With one of the richest legacies in the country, it is a living monument to the battle to win our nation’s independence. From the thousands of years of indigenous culture to colonial forefathers, the Constitution State has left indelible footprints in America’s heritage. Over half of the state’s towns date back to the 17th and 18th centuries. Connecticut has more than stamped its place in history, from Georgian architecture and revolutionary battlefields to seaside ports and pioneering railways. Get to know more about some of the oldest-founded towns in the state that are worth a visit.

Guildford

Founded in 1639, this hamlet is named after the area where the first settlers originated in England. Home to some of the oldest architecture in New England, Guilford is a town built on colonial heritage. With access to beaches, lakes, and mountains, there is something for everyone to explore.

The Town Green is located in the heart of Guilford and is the base for most of the town’s activities. Shops and farm-to-table eateries line the main street, locally called Route One. Be sure to stop at the Village Chocolatier. It has consistently been named the Top Confectionery in Connecticut and offers all cocoa treats. Guilford is very walkable, so take advantage of tours offered by resident volunteers. From legends about historical homes to their role in the Salem Witch Trials, you will have over 400 years of memorable stories.

The Hyland House is a perfect example of evolving colonial architecture. This saltbox-style building, built in 1713, is on the Registry of National History. Bishop’s Orchards Farm Market and Winery offers fun for the entire family. Run for over six centuries by the Bishop family, it has been servicing the Guilford community since 1871. Pick your fruits and shop for fresh-baked bread and pies after you have worked up an appetite exploring the nearby nature trails.

Windsor

This small village is one of the first English settlements in the state and is in the heart of Fairfield County. Named after Windsor, England, it was founded in 1637. Home to the first highway in Connecticut, it enabled trade with counties between Windsor and Hartford.

Built in 1921, the Windsor Historical Society house offers visitors the chance to be in the oldest-standing community in the state. With over four centuries of history to draw from, its exhibits always evolve to reflect the nature of the community around them. Vintage photographs and letters, along with guided narration, tell the storied heritage of this land.

Stop by the Vintage Radio and Communications Museum for a fun twist on history. With over 200 years of artifacts, guests can learn about how we interacted in the past. From Morse code to the smartphone, fascinating exhibits show us that we have come a long way electronically. The need to find ways to stay in touch with loved ones was universal. Grab a pint and shepherd’s pie at the Union Street Tavern. Reminiscent of old-time England, this pub in the heart of town has been a local staple for years. Enjoy the vintage photographs from over a century that line the walls.

Milford

This coastal city is nestled between New Haven and Bridgeport. Founded in 1640, its indigenous roots are reflected throughout the town. During the late 18th and early 19th centuries, portions of Milford broke off into their own incorporated towns, including Woodbridge and Bethany. Owing to its seaside location, its main industries were shipbuilding and oysters.

Spread across Milford Harbor sits The Eells-Stow House. Considered the oldest home in Milford, it is the former residence of Captain Stephen Stow, a medic during the Revolutionary War. The sea and salt air damaged much of the original structure, but in 1980, great efforts were made to restore it to its original glory. The Bryan Downs House is a six-room saltbox structure built in the late 1700s. Today, it’s home to a museum that includes Native American Collections and a mini Country Store.

The Devon Center offers shopping, restaurants, and Revolutionary War Monuments. Milford Green, which dates back to 1649, is considered one of New England’s largest downtown park areas. If theatre or open-air concerts interest you, then the Milford Arts Center is a must-see. Hosting year-round entertainment, this community-run organization sources most of its content from regional history and pop culture.

Deep River

Initially named Saybrook, this village was renamed in 1947 to commemorate the creeks that powered the mills in the original colonies. Founded in 1644, Deep River is part of the area locals call Tri-Town, including Chester and Essex.

In the mid-19th century, most of the ivory bought in the United States came through Deep River, earning it the name “Queen of the Valley” due to the extreme wealth brought in by his ivory trade.

The Deep River Freight Station, built in 1915, is a preserved example of twentieth-century train operations. Railfans will enjoy the anecdotal stories from the engineers who still manage the station for train rides and steamboats. It became a historical landmark in 1994.

Only a fifteen-minute drive away in Essex is one of the oldest continuously running inns in the country. Built in 1776, this magnificent structure has witnessed the Revolution, the Civil War, the Temperance movement, and more. Each room is boutique decorated to celebrate the heritage without sacrificing modern comforts.

Simsbury

Incorporated in 1671, this town was indigenous to the Wappinger group of tribes. Designed in 1892, Drake Hill Road Bridge is a popular spot for wedding and engagement photos. Spanning over the Farmington River, it’s one of the state’s finest examples of metal truss design. Up until this time, most bridges were made of wood or cement. The metal truss design allowed for more stability and flexibility in adjustment.

Simsbury abounds with architectural masterpieces. The Simsbury Center Historical Society provides maps and visitor information. With so many opportunities to immerse yourself in colonial history, you will be spoiled for choice.

Situated in Talcott Mountain State Park stands Heublein Tower. The original structure was built in 1810 but has been renovated four times over the past two centuries. It has six stories, bedrooms, and bathrooms, and the observation deck provides 360-degree views of the entire region. A classic example of Georgian architecture is the John Humphrey House, built in 1760 and open for tours. Now referred to as The Phelps Tavern Museum, the estate was the former home of Captain Elisha Phelps, one of the commanders of the Continental Army.

Spend the night at the Stanton House Inn. Family-owned and operated, the Inn was initially a private residence. Built by legendary New England architect Stanford White in the early 1900s, it is within walking distance of historic downtown Simsbury.

Wethersfield

Founded in 1634 by Puritans, Windsor is the oldest village in the state, although Windsor residents try to challenge that claim. Known for four witch trials, its rich heritage is felt throughout the village.

Old Wethersfield Historic District is on the National Register of Historic Places; over 50 houses date back to the Revolutionary War and 100 before the Civil War. The Joseph Webb House was the site of a five-day conference between George Washington and French Commander Rochambeau.

Mill Woods Park is the ideal place for a picnic, relaxing stroll, or community garden. During the warm months, there are outdoor concerts. In the winter, the pond freezes over and has been used as a skating rink. Plaques commemorate the area where Revolutionary soldiers set up encampments.

Shop on Main Street for authentic local flavor. Antique and specialty stores like Antiques on Main, Heart of the Country, and House of Images Gallery celebrate the heritage of Connecticut’s oldest town.

Stratford

Settled by Puritans in 1839, Stratford is unprecedentedly woven into Connecticut’s history. Unlike other towns on this list, many of its residents are directly related to the Puritan ancestors who migrated here from England.

With one and a half miles of beach on Long Island Sound, Stratford residents take advantage of the suburban community but with easy access to the coast. Lordship Seawell boasts great restaurants and hotels. Fishing and water activities are plentiful as well. Visitors can rent kayaks or canoes for the day at the visitor’s center. Stroll over to Stratford Point and Lighthouse for amazing views of the coastline.

The Stratford Historical Society takes its place in the nation’s founding seriously. With an extensive catalog of information to provide tourists, you will go away with a true sense of what it means to live in this hamlet. The Captain David Judson House is a little gem. Built in 1763, it is one of the finest examples of Georgian Colonial architecture in the entire state. Now open to the public as a museum, the stone structure houses artifacts and exhibits, all guided by period-costumed docents.

After working up a thirst head over to for artisanal lager at Two Roads Brewing Company. Influenced by their regional history , they make an effort to highlight the heritage and balance it with contemporary life in Stratford.

Connecticut is a year-round destination. Each season sets the ideal backdrop for a visit, whether it’s the fall foliage, snowy mountaintops, fields of wildflowers, or the sun reflecting off the whitecapped saltwater waves. However, Its undeniable history remains constant no matter what the forecast. From colonial homes to indigenous trails, the narrative of America’s humble beginnings is waiting to welcome you.