Not the Same Old Saybrook

Saybrook Point Marina.

The town of Old Saybrook, at the mouth of the Connecticut River, has seen some changes over the years, but the magic of its surrounding waters endures.

By Malerie Yolen-Cohen • Photography by Tom Richardson

Pulling into Old Saybrook, at the mouth of the Connecticut River, might leave you breathless—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 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.

Saybrook Breakwater Light guards the mouth of the Connecticut River.

Lovely Loop

Whichever marina you choose, it helps to have a bicycle to reach the shops, restaurants and boutiques of the downtown area, about 1 1/2 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.

Boaters at Saybrook Point Marina gather at the outdoor bar for frozen refreshment after a day on the water.

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. 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.

Lobster roll and truffle fries at Fresh Salt.

Rat Pack Days

History also inhabits the magnificent Saybrook Point Inn and Spa, which offers panoramic views of both the river and Long Island Sound. It encompasses a “green” marina, an outdoor heated pool, a restaurant, a community fitness center and two brand-new “boutique inn” additions.

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.

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.


Upriver Exploration

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 backwater creeks and coves, where you’ll feel like an early-American trader, surrounded by scores of wading birds, beaver, otter and other wildlife.

Old Saybrook boasts a large population of swans, which not everyone finds to be a good thing.

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.

The Baldwin Bridge launch facility.

Old Saybrook Names & Numbers

(860) 662-0358

Dockage, Moorings & Service

  • Saybrook Point Marina; (860) 395-3080
    Home to a luxury hotel and spa, Saybrook Point Marina can accommodate boats up to 200 feet. Amenities include complimentary cable TV and WiFi, shuttle service to town, bicycles, a fitness center, indoor and outdoor pools, a sauna, and hot tub, picnic areas with gas grills and ValvTect fuel.
  • Brewer Ferry Point Marina(860) 388-3260
    Transient boaters are welcome at this well-protected marina three miles north of river mouth. Amenities include a picnic area, pool, playscape, cable and WiFi, fuel dock, pump-out, ice, ship’s store, showers and laundry facilities.
  • Harbor One Marina; (860) 388-9208
    Located immediately inside the Old Saybrook breakwater, Harbor One can accommodate boats up to 150 feet. Also features a pool, laundry, showers, bathrooms, casual restaurant and shuttle service to town.
  • Ragged Rock Marina; (860) 388-1049
    Just past the railroad bridge and nestled inside a well-protected basin, Ragged Rock has transient slips, WiFi, cable, showers, laundry, picnic area and pump-out.
  • Between the Bridges Marina; (860) 388-1431
    Two miles from Long Island Sound. Offers transient slips, pool, WiFi, cable, newly renovated restrooms and showers, on-site restaurant, fuel dock, fish-cleaning stations, water and electric.
  • Oak Leaf Marina; (860) 388-9817
    Full-service boatyard just north of the I-95 bridge. Can accommodate boats up to 100 feet. Offers water, electric, showers, laundry, repair. Within walking distance of restaurants and a motel.
  • Island Cove Marina(860) 388-0029
    North of the I-95 bridge, Island Cove accommodates vessels up to 45 feet and features moorings, a dinghy dock, TV, WiFi, ice, showers, laundry, lounge/kitchen. Within walking distance of a local restaurant.

Launch Ramp

  • Baldwin Bridge (I-95 launch)
    Large, free state ramp with ample parking below the I-95 bridge. Can accommodate large boats.

Kayak Rental

  • Oyster River Kayak Adventures; (860) 918-2598
    Kayak and SUP rentals on the scenic Oyster River.

Where to Eat

  • Fresh Salt; (860) 388-1111
    Formerly Terra Mar, this highly rated restaurant at the Saybrook Point Inn and Spa offers a casual, clubby atmosphere with river views. Indoor and outdoor seating available.
  • Aspen; (860) 395-5888
    Upscale New American dining. Offers a wide selection of happy hour appetizers and beverages.
  • Liv’s Oyster Bar; (860) 395-5577
    Specializes in fresh oysters and other local seafood.
  • Penny Lane Pub; (860) 388-9646
    Cozy English-style pub with a cool neighborhood vibe.

Cool Shops

  • Harbor Books; (860) 388-6850
    Independent bookstore carrying wide selection of new and used titles.
  • Saybrook Recycled Furniture Etcetera; (806) 388-6180
    Thrift store that buys and sells various goods, including furniture, housewares, collectibles, and fun and useful items.
  • Tova’s Vintage Shop; (860) 395-1955 
    Glamorous old Hollywood dresses and gowns, rhinestones, designer costume jewelry, 1880s beaded bags, 1960s leather box purses, vintage hats and more.
  • Saybrook Country Barn; (860) 388-0891
    Upscale shops specializing in home furnishings and clothing.

Things to See & Do

  • Katharine Hepburn Cultural Arts Center
    Known as “The Kate,” the center hosts dance, theater, opera and film events in a cozy 250-seat auditorium.
  • General William Hart House; (860) 395-1635 
    Built in 1767, this preserved historic home is one of the earliest houses in Saybrook, the first settlement on the southern shore of Connecticut.

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