Saybrook Breakwater Lighthouse and Lynde Point Lighthouse are prominent Old Saybrook landmarks.

Pulling into Old Saybrook, at the mouth of the Connecticut River, might leave you breathless—but in a good way. Shortly after clearing the breakwalls guarding the mouth of the river, it doesn’t take long to appreciate why the Connecticut was designated America’s first “National Blueway” in 2012. Here, where the great river meets Long Island Sound, undeveloped coves and marshlands, bluffs and beaches merge to form a landscape worthy of an impressionist oil painting. Small wonder Old Saybrook has attracted boaters for 150 years.

There are no less than seven marinas in this small, coastal burg with a population of around 10,000. Saybrook Point and Harbor One are closest to the Sound; the rest are clustered a few miles farther upriver, around the I-95 and railroad bridges.

Whichever marina you choose, it helps to have a bicycle to reach the shops, restaurants, and boutiques of the downtown area, about 1 ½ miles from Saybrook Point and Harbor One (although both offer shuttle service to town), and roughly three miles from the marinas near the bridges. Plan an early-morning or late-afternoon ride on “The Loop,” a stunning ten-mile byway that traverses causeways, passes the Lynde Point and Saybrook Point lighthouses, and skirts reed-lined coves and waterfront neighborhoods. Riding during sunrise or sunset is particularly breathtaking, and the time when you’re most likely to find local artists by the roadside, ardently working at their easels.

The sprawling Saybrook Point Resort and Marina welcomes transient boaters at its large marina.

One of the neighborhoods you’ll see on this ride is the fancy Fenwick section of Old Saybrook, an enclave of shingled mansions overlooking Long Island Sound. For many years, Fenwick’s most famous resident was Hollywood star Katharine Hepburn, who lived in Old Saybrook until her death in 2003 at age 96. Ever down-to-earth (Kate did her own grocery shopping), no-nonsense, and fiercely independent, Hepburn was beloved by the community, which named the renovated Cultural Arts Center in her honor.

Hepburn was not the only strong, notable woman who lived in this shoreside town. The now-defunct Tissa’s LeSouk du Maroc Restaurant was once the 1790 General Store of the Humphrey Pratt Tavern, where, in 1824, the Marquis de Lafayette “made a purchase,” as it states on a prominent sign by the front door. In the early 1900s, the building became a pharmacy and soda shop run by Anna James, the daughter of an escaped slave and the first African-American woman to become a pharmacist in Connecticut. James, “the confidant and conscience of the community,” was the only woman in her class at the Brooklyn College of Pharmacy, Class of 1908. She took over her sister’s and brother-in-law’s drugstore in 1922 and retired in 1967 at the age of 81.

History also inhabits the magnificent Saybrook Point Inn and Spa, which offers panoramic views of both the river and Long Island Sound. It encompasses the Saybrook Point Marina, an outdoor heated pool with tiki bar, a restaurant, a community fitness center and two “boutique” accommodations.

Due to its striking location, nestled among wildlife-rich coves and saltwater marshes at the mouth of the Connecticut, Saybrook Point has been luring tourists since the late 1870s, first as a small inn called the Pease House, then as the Rat Pack hangout, Terra Mar.

Katharine Hepburn was Old Saybrook’s most famous resident.

The hotel drew Frank Sinatra, Jane Mansfield, Ted Kennedy, Tom Jones, and a slew of celebs to its two large outdoor pools and big-yacht marina. In the warm months, Terra Mar was “Las Vegas meets Miami Beach,” attracting gamblers, gangsters, and, finally, federal law-enforcers, who cracked down on the illegal activities and effectively put Terra Mar out of business until its rescue, overhaul, and rededication as the Saybrook Point Inn in the early 1990s.

Whether you keep your boat in Old Saybrook for the season or just a few days, the town is the perfect home base from which to explore other destinations on the lower Connecticut, including Essex, Deep River, Chester, and Portland. Or simply spend some time soaking in the beauty of the river itself, whose undeveloped banks remain much as they did when Europeans first settled here. If you have a small boat or kayak, take time to poke around the creeks and coves, where you’ll feel like an early-American trader, surrounded by scores of wading birds, beaver, otter, and other wildlife.

Naturally, Old Saybrook’s location at the mouth of the river also puts boaters within easy reach of other coastal daytrip or weekend destinations. It’s a quick cruise across the Sound to Shelter Island, Greenport, Sag Harbor, and other East End hot spots, while the towns of Clinton and Niantic are equally close by and worth a visit.

Whether you choose to head upriver or into the Sound, or simply stay put and check out the town’s shoreside offerings, Old Saybrook has plenty to keep you entertained—and coming back for more.