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Living in Old Saybrook: The Oldest Settlement on the Connecticut Shoreline

The area that is now known as Old Saybrook, Connecticut, has a long history dating back before the arrival of Europeans when it was inhabited by the Algonquin and Nehantic tribes. Eventually, the Pequot tribe overtook the area, which is how it stayed until a Dutch ship ventured into the region in 1614.


Photograph of lighthouse on the water in Old Saybrook

By 1623, a Dutch colony had been established in the region, although it did not work out, and the settlers returned to New Amsterdam within a few months. Despite this failure, the region remained attractive to settlers, and the English set up another colony in 1635.

The new colony would expand to cover present-day Essex, Deep River, and Westbrook, as well, and has remained a fixture in this part of the country ever since. Living in Old Saybrook means immersing yourself in all kinds of history, in addition to the other great activities throughout the region. Here's what you should know about living in Old Saybrook, CT.

Where to Work

Residing in Old Saybrook provides you with constant access to the beach, as the town is full of them. As a result, there's a fair amount of tourist traffic here, especially in the summer, which means a lot of employment is in the service industry.

Many people work in hospitality in Old Saybrook, as the area's hotels and restaurants need plenty of employees in the busy months. There are also health services, marketing, education, and manufacturing jobs within the town, providing plenty of opportunities. Retail is an option, as well.

Professionals will find law, accounting, and insurance offices in Old Saybrook, and there is a large grouping of car dealerships on the Middlesex Turnpike.

As you can see, despite the town having a population of only 10,000 people, there are plenty of places to work in Old Saybrook.

It's also important to note that you can easily live in Old Saybrook while working in a larger center like New London or New Haven, as both are about a 30-minute drive away.

Parks, Beaches, and Outdoor Activities

We mentioned that beaches are everywhere in Old Saybrook, and that's the truth, as you'll find seven major areas to explore along the shoreline.

Two of the most popular are Harveys Beach and Town Beach, which sit just south of downtown about a block from each other. Both have ample parking areas and change rooms, making them popular with tourists in the summer.

Many of the other beaches, such as Great Hammock, Knollwood, Cove, Plum Bank, Indiantown, and Chalker, sit in residential areas and don't have much parking. If you happen to buy a home in one of these neighborhoods, you'll love these shores because their locations make it difficult for summer traffic to reach while being within walking distance for locals.

Outside of the beaches, you'll discover a great hiking area called The Preserve, which, at 963 acres, is the largest unprotected coastal forest between Boston and New York.

There's also Fort Saybrook, a historical park located on the site of the original colony from 1635. As you walk through the fort, you'll come across signs that explain the region's history, and you can even continue to the town's marina.

Dining and Shopping Options

Despite its small size, Old Saybrook is packed with great restaurants. One drive down Boston Post Road or Main Street means seeing dozens of dining options, including pizza places, Mexican restaurants, pubs, cafes, breweries, fast food chains, and diners.

Anything you could ever want to eat, you'll find it in Old Saybrook.

The shopping scene isn't quite as dynamic, although you'll find Ocean State Shopping Center, Old Saybrook Shopping Center, and Elm Street Shopping Center within a couple of blocks of each other on Boston Post Road. There are also some antique shops on the Middlesex Turnpike and some small, local retailers on Main Street.

The School System

There are three schools within the Old Saybrook public district: Kathleen E. Goodwin Elementary School, Old Saybrook Middle School, and Old Saybrook High School.

Students will attend Goodwin Elementary School between kindergarten and grade four, before heading to the middle school for grades five through eight and finishing their education at the high school.

For younger children, you'll find The Sherwood School and The Children's Tree Montessori School, which are preschools. The Sherwood School has a variety of different options available for young kids, including after school childcare, while The Children's Tree Montessori School is a private facility with a complicated application and enrollment process.

The town is also home to Saint John School, a private Catholic school for kids between preschool and grade eight. Other private school opportunities are available in neighboring communities, as well.

Public Transit

You'll find it easy to get around once you live in Old Saybrook because there are numerous public transportation options. The key to local area transportation is 9 Town Transit, which operates Route 1 between Madison and Old Saybrook, Route 2 between Chester and Old Saybrook, and Route 3 between New London and Old Saybrook. Since all of the buses meet in Old Saybrook, it's a regional hub for public transportation.

There are numerous bus stops throughout Old Saybrook, as well, so you can use the service to get from one end of town to the other.

In addition to the bus, there's Old Saybrook Station, which is a stopping point for the Shore Line East commuter train and Amtrak. With Shore Line East, you can take the train west to New Haven or east to New London, and there are further routes available from those cities. Amtrak serves destinations all over the East Coast, and throughout the country, so you can access pretty much any major center from Old Saybrook.

Buying a Home in Old Saybrook

Living in Old Saybrook will bring plenty of positives to your life, as the town is a full-on beach destination that has a few sandy areas usually frequented by locals. It's also close enough to major cities that you can reach them quickly, yet far enough that you can spend your time away from the bustle.

If you're looking to buy a home on the Connecticut Shoreline, you could certainly do worse than the area's oldest continually inhabited settlement, Old Saybrook.