11 Small Town Things to do in Old Saybrook CT: Hepburn’s Haunt on the CT River

Situated at the mouth of the Connecticut River where it meets Long Island Sound, Old Saybrook CT has drawn vacationers and celebrities for 150 years. Wavery-voiced actress, Katharine Hepburn lived in the Fenwick neighborhood until she died in 2003.

View from room at Tall Tales, Saybrook Point Inn and Spa, CT

Out on “the point,” The Saybrook Point Inn and Spa also encompasses Tall Tales, next door to Three Stories. Both are “Boutique Inns,” and serve as alternatives to the hotel’s already luxurious accommodations.

Learn about Saybrook Point’s earlier incarnation as Terra Mar, frequented by Hollywood luminaries and gangsters, and some cherished African American history, on this surprisingly down-to-earth but high-class Connecticut coastal Getaway.

On the water – Old Saybrook for sure is one of our Best Romantic Getaways in CT. Check out the roundup of our favorite romantic destinations in Connecticut and be inspired.

Where Is Old Saybrook CT?

Old Saybrook, Connecticut, is a charming coastal town located in Middlesex County, situated along the picturesque Connecticut shoreline. Positioned at the mouth of the Connecticut River, Old Saybrook offers a delightful blend of coastal beauty, maritime history, and New England charm. It is conveniently located midway between the cities of New York and Boston, making it an accessible and inviting destination for travelers seeking a tranquil seaside escape.

This historic town is known for its scenic beaches, a vibrant downtown area with boutique shops and restaurants, and a rich cultural heritage that includes the iconic Katharine Hepburn Cultural Arts Center. Old Saybrook’s coastal location and nautical ambiance make it a beloved spot for those looking to immerse themselves in the natural splendor and timeless allure of New England’s shoreline.

Things to Do in Old Saybrook CT

Kate Hepburn's Neighborhood, Old Saybrook CT
Kate Hepburn’s Neighborhood, Old Saybrook CT

DO: Drive Around Fenwick

Kate was Annie Hall without the neurosis. She wore pants! She was beautiful, witty, and a clever verbal sparring partner with each of her leading men.

Katharine Hepburn, the legendary actress, was a hero and role model for women who were not afraid to be smart. And she lived right here, in Old Saybrook, as she couldn’t stand the fake, striving, Hollywood scene.

Kate came by her strong feminist views honestly. Her mother, also named Katharine Houghton Hepburn, was influential in the Women’s Suffrage movement. (The Sr. Kate co-founded the American Birth Control League with Margaret Sanger in the 1930’s).

Lynde Point Light, Old Saybrook CT
Lynde Point Light, Old Saybrook CT

The Hepburns lived in Hartford CT, but had a summer home in the Fenwick section of Old Saybrook. That home was washed away during the Hurricane of 1938. So Kate rebuilt a larger house on the same site. She lived here until her death at age 96.

Known in town as down to earth (she did her grocery shopping), no-nonsense, and fiercely independent, Kate was beloved by the community. In her honor, the people of Old Saybrook named the renovated Arts Center after her.

Old Saybrook Sunset
Saybrook Cove at Sunset

BIKE: “The Loop” 

This ten-mile loop on Route 154 crosses causeway bridges, affords dead-on views of two lighthouses (Lynde Point and Saybrook Point Lighthouses), and traverses reed-framed, salt-marsh coves and waterfront neighborhoods. Peddling during sunrise or sunset is particularly beguiling.

The Kate, Old Saybrook CT
The Kate, Old Saybrook CT

VISIT: “The Kate” – aka Katharine Hepburn Cultural Arts Center

The Kate hosts dance, theater, opera, and film events in a cozy 250-seat auditorium. Even if you don’t see a show, feel free to pop in.

LOCAL NOTABLE: Anna James/James Pharmacy

Kate Hepburn was not the only strong, notable woman in this little Connecticut Shore town. What is now a new boutique B&B and Gelato Shop was once the 1790 General Store for the Humphrey Pratt Tavern. (In 1824, a historical marker proclaims, the Marquis de Lafayette “made a purchase” here.)

In the early 1900’s the store was a Pharmacy/Soda Fountain, run by Anna James. James, the daughter of an escaped slave, was the first African-American woman to become a pharmacist in Connecticut.

Anna James Pharmacy, Old Saybrook CT
“Miss James” of James Pharmacy, Old Saybrook CT

James was the only woman in her class at Brooklyn College of Pharmacy, Class of 1908. She took over her sister and brother-in-law’s drugstore in 1922 and retired in 1967 at the age of 81.

Old Saybrook has always had a mostly white population. But in the mid-1900s, Anna, known affectionately as “Miss James, was considered the “confidant and conscience” of the community.

Owners of the inn have preserved the charming wood apothecary drawers and the pharmacy’s original 1896 Soda Fountain with Vermont Granite counter.

James Pharmacy Apothocary Drawers
James Pharmacy Apothecary Drawers, Old Saybrook CT

For a time, James employed her sister’s daughter, Ann Petry, who obtained her Pharmacist license before finding fame and fortune as a novelist.

Petry’s classic American novel, The Street (1946), was the first book written by an African American author to sell over a million copies. Its theme, about a young hardworking black mother struggling to raise her child in 1940s Harlem, still resonates today.

TOUR: General William Hart House, Home to Old Saybrook Historical Society

What was the lifestyle of the rich and famous (or not so famous) on the Connecticut Coast back in 1767? A tour of the General William Hart House provides a good idea of how a prosperous trader-merchant and his family lived during Colonial times.

WANDER: Fort Saybrook Monument Park

Next to the Saybrook Point Resort and Marina, Fort Saybrook Monument Park at the mouth of the Long Island Sound (where it meets the Connecticut River) has gone through many iterations since it was built as New England’s first fortification in the 1630’s.

By the mid 1800’s the grounds were leveled for the Connecticut Valley Railroad’s roundhouse and Turntable, and some of those remnants still remain. You can read all the information panels while strolling paved paths and boardwalks at this 18-acre park. Or just gaze out at the place where the river meets the Sound.

DO: Mini Golf at Saybrook Point

You won’t find a prettier place to putt-putt than at the seaside Mini Golf at Saybrook Point. Go in a late afternoon golden hour in summer, and you won’t even care about your score – or even keeping score. The little course is pristine, there’s ice-cream, yachts motor right offshore, and all is right with the world.

Sanno Spa at Saybrook Point Inn and Spa, Old Saybrook CT

SPA: Spa @ Saybrook Point Resort and Marina

Excellent massage therapists know how to work the kinks out of even the most tense, stressed-out bodies at Saybrook Point Resort and Marina’s in-house full-service spa.

Though signature treatments are splurgy delights, Sanno’s staff excels in the standard 50-minute Swedish Massage which leaves skin baby soft and muscles supple.

If you stick around for another treatment, go for the 80-minute “Ocean Memory”($169) – which incorporates a “marine based oil massage” with tingling algae mouse moisturizer. Or opt for The Signature “Kate”. This treatment embraces Hepburn’s love of roses, with a body scrub, rinse and head-to-toe moisturizer.

Harbor Books, Old Saybrook CT

SHOP: Harbor Books

A vanishing breed, independent bookstores should be supported and cherished. So, while meandering up and down Old Saybrook Main Street – or after a matinee at The Kate, be sure to peruse the stacks at Harbor Books. It’s small but contains a great selection of both old and new books.

BEACH: Harvey’s Beach

Harvey’s is small, and quiet – so best for families with little ones who love to explore the tide pools.

Saybrook Point Marina Old Saybrook CT

BOATERS: Saybrook Point Resort Marina

Transient boaters are not only welcome at the Saybrook Point Resort Marina – they are coddled. Those arriving by sea can use many of the Inn and Spa facilities (including the fitness center, jacuzzi, and pools), fuel up, and join the throngs of happy people at the new outdoor Marina Bar.

Find the marina via two landmarks. The first, a larger Lynde Point Lighthouse then the much smaller Lighthouse Suite atop Saybrook Point Marina Inn’s dock master’s office. The 125 slips can accommodate boats 25-225 feet in length.

Things To Do Near Old Saybrook Ct

Spend a day in Niantic-East Lyme lying on the sand at Rocky Neck State Park: just a 15 minute drive North on I-95

It’s a quick five miles from Old Saybrook to the Florence Griswold Museum in Old Lyme CT. On the National Register of Historic Places, the Museum celebrates the 19th Century origins of the American Impressionist Movement, as Miss Griswold ran her home as a boarding house for starving artists, who painted on her walls as payment for room and board.

It’s 10-15 minute drive to the engaging Connecticut River Museum in Essex CT. Did you know that the very first submarine, The Turtle, was built nearby in 1776 to bomb British ships at anchor? Find out there.

Restaurants in Old Saybrook CT

EAT/FINE: Fresh Salt @ Saybrook Point Inn

Formerly Terra Mar Restaurant, Saybrook Point Inn’s in-house restaurant is now the clubby Fresh Salt. A bank of windows overlooks the marina. Prints of sailing ships line dark wood walls. An illuminated salt-water fish tank adds color pop. And the wood-burning fireplace offers cozy warmth in winter.

Liv's Oyster Bar, Old Saybrook CT

EAT/FINE: Liv’s Oyster Bar

Liv’s Oyster Bar, in an old repurposed movie theater, is known for its Raw Bar. (The display of chilled oysters is situated where the concession stand used to be). A favorite local dining spot, you can also find a range of surf and turf items on the menu.

Monkey Farm Restaurant, Old Saybrook CT

EAT/CASUAL: The Monkey Farm

The Monkey Farm, formerly an 1800s stage road inn on the Boston Post Road, was purchased by Harry Corning in 1968 as the SayBrook Inn. In 1978 Corning renamed it, The Monkey Farm. There were never any live monkeys here, as some rumors have it.

The place, now a burger and salad spot, got its name for either various sports teams or for the reputation of one of the owners who would toss the keys to a patron whenever he took off for Vegas, leading one to comment, “They’ll let anyone work here. This place is nothing but a monkey farm.”

Monkeys or not, this roadhouse has been an Old Saybrook icon for decades. The kitchen was renovated in 2006 and currently, Harry’s three kids are in charge.

Saybrook Point Inn Tall Tales Three Stories CT

Hotels in Old Saybrook CT

STAY: Saybrook Point Resort and Marina

The Saybrook Point Resort and Marina, perched at the end point of a Long Island Sound peninsula, encompasses a “green” marina, an outdoor heated pool (hot and steaming in the snow-cold days of winter), a large indoor pool, and an excellent Spa. The in-house restaurant, Fresh Salt, affords dazzling panoramas. The community Fitness Center is a true perk for guests.

Across the street, two grand Victorian homes were transformed into “boutique inns:” Tall Tales, and Three Stories Guesthouse.

In addition, all the buildings are “green.” Each property recycles its rainwater – which funnels from gutter to cistern – to water plants. Each room is equipped with infrared thermostats that determine if you are there or not (and if not, turns down the heat or ups the AC accordingly).

And year round outdoor and indoor pools are heated with co-generation energy (utilizing a diesel engine). To say that The Saybrook Point Inn and Spa is on the forefront of environmental hospitality is an understatement.

First Impressions 

Terra Mar Hotel, Old Saybrook CT
Terra Mar Hotel during its heyday in 1960’s, Old Saybrook CT

The Saybrook Point Resort is quite an about-face from the hotel that stood on this site in the 1960’s and 70s. Due to its striking location at the mouth of the Connecticut River, Saybrook Point has been luring tourists since the late 1870s: First as The Pease House and then Rat Pack favorite, Terra Mar.

Had Terra Mar survived, it would have been an ideal location for an episode of Mad Men. Fifties Modern, three large outdoor pools, a big-yacht marina – Terra Mar was favored by the likes of Frank Sinatra, Jane Mansfield, Ted Kennedy, and Tom Jones.

In summer, Terra Mar was Las Vegas meets Miami Beach, attracting gambling, gangsters and finally, The Law, which cracked down on illegal activities and effectively put Terra Mar out of business. (Apparently, what happened in Old Saybrook didn’t stay in Old Saybrook).

Saybrook Point Inn, Lobby
Saybrook Point Resort and marina, Main Lobby

Now, in contrast to the Terra Mar, the lobby of Saybrook Point Inn’s canary yellow main building is cozy and thick with antiques. A bank of French doors opens onto an outdoor deck.

In warmer weather, this deck vibrates with wedding parties, corporate groups and anyone who enjoys a good meal overlooking a collection of sleek yachts.

Boutique Lodgings at Saybrook Point Inn

Three Stories at Saybrook Point Inn, Front Door
Three Stories at Saybrook Point Resort and Marina, Front Door


The three-story (get it? Three Stories?) 1892 Italianate home of railroad engineer, William Vars, is now a luxury “Boutique Inn.” Choose from eight renovated rooms – each one elegant and luxurious in its way.

Katherine Hepburn Suite Bathroom Saybrook Point Inn CT

Several, like the Katharine Hepburn Suite, offer seaside balconies from which, even in the freezing days of winter, you’ll find magnificent sunrise and sunset views.

View of Water from Tall Tales Guest House Saybrook Point Inn

Each suite is named after a local notable: Kate Hepburn, of course, but also Anna James, William Vars, and Saybrook Point owners Mary Tagliatela and her son, Steven.

Three Stories Guesthouse Common Areas

Breakfast gathering table at Three Stories, Saybrook Point Inn
Breakfast gathering table at Three Stories, Saybrook Point Inn

Three Stories’ main floor is inviting and warm, with long dining table, an electric fireplace and plenty of room to do puzzles or sit and talk.

Billiards Room Three Stories at Saybrook Point Inn
Billiards Room Three Stories at Saybrook Point Inn

Downstairs, the billiards room and large flat screen TV is popular with family or friends reunions. 

Three Stories Lobby, Saybrook Point Inn
Three Stories Lobby, Saybrook Point Inn

The Hepburn Suite’s massive bathroom features black and white basket-weave mosaic floor, large multi-head glass shower and just the faintest whisper of lilac paint above white wainscoting.

Hepburn Suite Saybrook Point Inn

A high four-poster bed faces an electric fireplace and a sitting area with plenty of plush seating. I loved the selection of Kate Hepburn photography books on several shelves, and discovered that she would have much preferred sitting on the floor!

William Vars Suite at Three Stories
William Vars Suite at Three Stories Guest House, Old Saybrook CT

Three Stories has a room for every taste – including William Vars Room – the former owner’s bedroom. Designed in blues and masculine accoutrements, it’s perfect for a guy who wishes to avoid pink, chintz, or any stereotypical B&B décor at all costs.

Anna James Room at Three Stories
Anna James Room at Three Stories, Saybrook Point Inn, CT

My personal favorite is the Anna James Room. This suite with two Queen beds is best for a girlfriend getaway. Three Stories has two such rooms – both stunning.

Common Area, Tall Tales, Saybrook Point Inn and Spa, Old Saybrook CT


With a French Country Contemporary decor, the 6-room Tall Tales Guesthouse is slightly more casual than Three Stories next door. But it’s equally eye-catching and eminently lovely and dreamy when it comes to bed comfort.

Like its sister property, Tall Tales features different rooms for different tastes. There’s one with bold red walls, others dressed in pastels, and one with two queen sized beds perfect for a friend getaway.

Tall Tales Guesthouse Rooms and Common Areas

Guest Room, Tale Tales, Saybrook Point Inn and Spa, CT

The delightful decor of all rooms and common areas throughout the hotel complex comes from the creative mind of interior designer, Lisa Silver, who sources one of a kind furniture and accessories from “all over.”

Double Room, Tall Tales, Saybrook Point Inn and Spa, CT

Arguably, the most striking piece is a three-tier lamp that hangs over the parlor dining table, crocheted with tiny creme-colored wampum. I wasn’t the first guest who wanted to take it home. 

Billiards at Tall Tales, Saybrook Point Inn and Spa, Saybrook Point, CT

Like Three Stories, this building has a billiard table for all to use. In this case, it’s on the second floor in the common area between two guest rooms. Coffee and tea is available 24/7. And, in the morning, you can arrange for staff to deliver a light breakfast to the guesthouses.

Of course, you could always walk across the street for a full breakfast at Fresh Salt. But on nasty days, who’d want to.

Health and Wellness At Saybrook Point Inn

Saybrook Point Inn indoor pool
Saybrook Point Inn indoor pool

Health Club/Fitness Center

Saybrook Point Inn’s fitness room is much larger than most. That’s because it’s also a fitness center and health club for the community at large. So, feel free to “crash” a class – Aqua, Tai-Chi, Zumba, Spin, Pilates or Yoga.


  • Malerie Yolen-Cohen

    Malerie Yolen-Cohen is the Author of the cross-country travel guide, Stay On Route 6; Your Guide to All 3562 Miles of Transcontinental Route 6. She contributes frequently to Newsday, with credits in National Geographic Traveler, Ladies Home Journal, Yankee Magazine, Shape.com, Sierra Magazine, Porthole, Paddler, New England Boating, Huffington Post, and dozens of other publications. Malerie’s focus and specialty is Northeastern US, and she is constantly amazed by the caliber of restaurants and lodging in the unlikeliest places.

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