Old Saybrook, the oldest of The Shoreline’s many towns, was originally home to the peaceful Algonquin Nehantic Indians — until they were conquered by the Pequots, “a warlike tribe from the north,” in 1590. From that point on the history becomes quite complex, involving an early 17th century Dutch settlement at Saybrook Point, which lasted only a few months, and conveyance of the land in 1631 through a deed known as the “Warwick Patent,” signed by as many as 15 British patentees, who, in 1635, named John Winthrop, Jr., the first Governor of the Connecticut Territory.

Upon learning that the Dutch had not given up on thoughts of establishing a colony on Saybrook Point, Winthrop swiftly engaged Lieutenant Lion Gardiner to build a fort equipped with two canons there — and to lay out a small town. Upon arriving to see the progress of that effort, he named the new settlement Saye-Brooke, after English aristocrats. Eventually, Saye-Brook became Saybrook and the first of the Saybrook Colony settlements, which eventually included Chester, Deep River, Essex, Lyme, Old Lyme and Westbrook, all of which are now separate towns.

Since then, Saybrook has evolved into the Lower Connecticut Valley’s center for commercial, retail, and small manufacturing, as well as one of The Shoreline’s most popular places to live and vacation. Visitors often wonder how this charming little town has managed to remain a charming little town — free of the industry, wharves, and warehouses common to similar ports — given its spectacular location at the mouth of the largest river ecosystem in New England and a 16-mile coastline on the Sound. But the answer is surprisingly simple. Indeed, it’s no deeper (pun intended) than the wide sandbar that has impeded navigation inland from Colonial days to the present.

Route 154 along Main Street is home to the town’s most intriguing independent stores and restaurants, so a great way to start the day is with a really tasty breakfast at Mirsina’s. Then it’s on to do some shopping at Saybrook Home. Formerly, Saybrook Country Barn, it still offers a wonderful selection of home furnishings and women’s wear. In addition, this route offers such notable eateries as Liv’s Oyster Bar and the Penny Lane Pub, as well as the Katharine Hepburn Cultural Arts Center, located in the elegant old Town Hall and usually referred to simply as The Kate, making this part of town its own night out. And in late July, thousands converge on the Saybrook Green for the Old Saybrook Arts & Crafts Festival.

Beyond the center of town are scenic side roads, such as North Cove Road, leading not only to some of the prettiest homes on The Shoreline but to breathtaking views of the marshes and the sea. On Bridge Street is Harbor One Marina and Liv’s Shack, where the lobster rules are awesome. And down at the end of College Street are the parks at Saybrook Point, Captain Pete’s Sea Sprite Sport Fishing charters, and the sumptuous food, luxury lodgings, and spa at the Saybrook Point Resort & Marina.

Those traveling by land might enjoy a tour of the Fenwick, a tiny borough just across the causeway over South Cove, where Old Saybrook’s most famous resident, the late actress Katharine Hepburn, spent a great deal of time — her family’s sprawling “cottage” a perfect refuge from the world. A few of the several lanes in the borough are marked as private drives, but anyone can sign up for a tee time at the Old Saybrook Fenwick Golf Club, a 9-hole par-34 course.

Continuing westward on the Maple Avenue section of Route 154 takes one through the Fenwood neighborhood, past Knollwood Beach, and on to an outstanding panorama of sea and sky. Beyond that, Great Hammock Road threads its way through the golden marshes and tidal estuaries that have put Old Saybrook on the Nature Conservancy’s list of the Last Great Places on Earth.

Up in the northern reaches of town, Route 154 and Essex Road stretch past the Otter Cove neighborhood north of Ferry Point and the Baldwin Bridge, leading on to Old Lyme. The roads here reveal more of Old Saybrook’s lovely homes, along with exceptional views of the river at one of its broadest points. And north of Route 1 on Ingham Hill Road is Great Cedars Conservation Area, with marked trails open to the public. This peaceful site is contiguous to a pristine woodland tract that is among the very few intact coastal forests in New England.

Jennifer Cardinal Photos