Old Saybrook, Conn., wouldn't win an award for best beach destination, but its under-the-radar status and low-key vibe are exactly why travelers should visit this charming, small town situated on the Connecticut coast.
History buffs and naturalists will enjoy this well-heeled place with equal pleasure. Getting there is an easy drive from Boston or New York—100 miles up or down Interstate 95—and it's an ideal weekend getaway for residents or travelers in the region. A suggestion: Leave young ones at home and treat this adventure as an adults-only escape.
Check in at Ashlawn Farm Coffee, a dairy farm-turned-roastery near Old Saybrook's Train Station and the local place to grab a cup of joe. Coffee cognoscente can try a pour-over with, say, Ethiopia Yirgacheffe Konga beans.
Like much of the Northeast, Old Saybrook is steeped in Colonial history, but offers details all its own. Because of the land's position at the point where the Connecticut River meets the Atlantic Ocean, the area was seen as valuable and fought over by native Pequots, the Dutch and the English before it was settled by the English and named for Viscount Saye (William Fiennes) and Baron Brooke (Robert Greville) in the early 1630s. The English ultimately sent Lion Gardiner to build a fort in Saybrook to protect the colony. Today, you can explore the site of Saybrook Fort at the 17-acre Old Saybrook Monument Park. Along with informational reader boards, there is a memorial statue of Gardiner.
Fort Commander Colonel George Fenwick followed Gardiner as governor of the Saybrook colony. His wife, Alice, known as Lady Fenwick, became a pillar of the community before dying in childbirth in 1645. For locals, she's a legendary heroine who today rests interred at historic Cypress Cemetery, just down College Street from Monument Park. Although this isn't her original gravesite—the body was exhumed and moved in 1870—a sandstone monument surrounded by wrought iron marks her remains today.
Visitors to the cemetery can also note a large plot of land free of stones except for two—and there are no bodies buried here. These stones commemorate the nearby founding and operation of The Collegiate School in 1701, aka Yale University, before it moved to New Haven in 1716 and got quite famous as one of the country's top Ivy League institutions.
Main Street and Boston Post Road are Old Saybrook's hopping main drags, so plan to spend an afternoon here. Penny Lane Pub boasts a homey, pub-style atmosphere and a front patio that makes for great people-watching served alongside pints of Boddington or mojitos made with fresh mint from the kitchen's garden. Food options are hearty, including a turkey Reuben, the Oxford Circus vegetable wrap and fish and chips. Discover dessert at James Soda Fountain, a historic former general store then pharmacy run by Connecticut's first black female pharmacist (circa 1917), where you can now order New York egg creams and ice-cream sundaes—the signature Miss James' Dusty Rhodes is delectable as vanilla ice cream, hot fudge, whipped cream and malt powder. Flavors run the gamut from chocolate and buttercrunch to Rockin' Moroccan, a fragrant blend of orange blossom, cinnamon, dates and almonds that is a sweet tie-in with Tissa's Le Souk du Maroc, the Moroccan cafe that shares space with James'.
For explorers on foot or bike, two different, but equally gorgeous, neighborhoods offer soft sightseeing adventures. The tiny historic district of North Cove dons an old-money energy and has its own yacht club. Across an inlet from South Cove, the borough of Fenwick is a verdant, expansive (and labeled "private," but proceed anyway) area off Nibang Avenue that is home to a golf course and posh mansions with panoramic views of Long Island Sound. Actress Katharine Hepburn notably lived here throughout her life.
Old Saybrook's cultural events often happen at the Kate (formally, The Katharine Hepburn Cultural Arts Center). In the evenings, the stage affords concerts or theatrical performances, but during the day, anyone can tour the 100-year-old town hall-cum-theater and browse the small museum dedicated to Hepburn's career.
The eco-savvy set should appreciate that Old Saybrook goes to great lengths to protect its ecological environments, largely tidal wetlands, coastal forest and the Connecticut River estuaries. Down on the point, Old Saybrook Monument Park features six acres of marshland with special viewing platforms where you can observe a dozen species of nesting birds. As well, Bridge Street causeway shows off nesting and feeding areas for herons, egrets, swans and bald eagles perched in and around South Cove. Across town, vernal pools, swamp, streams and hiking trails occupy 1,000-acre woodland The Preserve, making it a great place to spot more migratory birds, amphibians and mammals like bobcats.
Although it costs between $10 and $20 (9 am and 4 pm) to park at Harveys Beach, it's worth it for a few hours relaxing by the shore, as lapping waves draw you into a full trance. Don't: Expect white sand and clear water. Do: Have fun examining the vast, pebbled sand bar that appears at low tide, out past the egret fishing in grassy, shallow waters for his lunch.
If you're looking for a place to stay, book a night at Saybrook Point Inn & Spa. The elegant inn perches on land that juts out into the river and the Long Island Sound, and the views from here couldn't be more spectacular. Attention to detail is paramount, from the staff who have incredible name recall to the artist-carved sea creature wharf pilings along the inn's marina. While the main inn building features upwards of 80 decadently decorated guestrooms, across the street the inn's year-old Three Stories Guest House serves up a B&B experience complete with afternoon coffee and biscotti, a billiards room-slash-man cave, and an open-air roof deck with a fire pit. Each of the eight rooms is named for a local historical figure, which you can learn about upon arrival.
Saybrook Point Inn restaurant Fresh Salt reigns as one of Old Saybrook's most proficient stops for dinner. Seafood, of course, is the thing to order. The raw bar features an everchanging selection of native oysters, day boat wins from local fishing boats, seasonal entrées like the signature cioppino and Point Judith calamari, and two styles of lobster roll (Connecticut with warm butter, or Maine chilled with mayo). Best of all: Prices are reasonable considering those to which Bostonians and New Yorkers are accustomed.
Make time to stroll along the harbor walk, which wends its way from Saybrook Mini-Golf ($5 per round) to the inn's bustling marina and post card perfect snapshots of sailboats, fishermen on piers, the artist colony of Lyme, and both Lynde Point Light and Saybrook Breakwater Lighthouse.
Old Saybrook features alternatives to history and nature, of course, namly in the form of retail and wellness therapies.
An intense Swedish massage administered at the inn's Sanno Spa works out all the kinks.
And as for shopping options, Fromage is worth a visit to load up on unique cheese, gourmet food and chocolate imports. Harbor Books sells used books for as low as a dollar each; travel memoires like Peter Mayles' "A Year in Provence" make for applicable reading materials over this weekend, especially when read from the private balcony of your room at Three Stories. The Saybrook Country Barn complex features 17 different interior boutiques, from upmarket clothing to candles to interior design services. Also onsite, The Ambrose Whittlesey House on the National Register of Historic Places, and luxe-cas Aspen restaurant—order the coffee-barbecue pork spring rolls, for sure. At some point during your visit, treat yourself to Pursuit of Pastry's soft, sugared baked doughnut. It's so worth the calories.
If you're searching out an optimal vantage point at sunset, walk over—or borrow one of the inn's bikes—to the Bridge Street causeway and prepare for a gorgeous way to end your day.