Guilford CT: Seeds of “Offbeat” Northeast

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WHY GO: Believe it or not, the unusual history of Guilford CT became the impetus for the Getaway Maven’s focus on quirky destinations.

Guilford borders Stony Creek and the Thimble Islands, an abundance of fanciful pink granite isles and outcroppings that create an otherworldly landscape. Known now for its artsy boutiques, a celebrity-favored outdoor restaurant and the oldest stone home in New England – which makes it, of course, a low-key getaway – Guilford has a rather odd and bloody past.

Neighborhood in Guilford CT named after the severed head of a Tribal Leader

Offbeat History of Guilford CT

THE OFFBEAT TRIVIA THAT STARTED IT ALL: Sachem’s Head. As I turned into the Sachem’s Head section of town with a Guilford historian, I’d assumed that this “headland” was so named because it juts out into the Long Island Sound.

But I soon learned that Sachem’s Head refers to the decapitated head of a captured Pequot Tribal Chief – the Sachem – placed by Colonial Brits in the fork of a shorefront tree after a territorial skirmish in 1637, warning other tribes of their fate should they retaliate. Strange that a whole neighborhood in Connecticut still bears the name of a severed head.  

Even stranger, a picture-book yellow cottage nestled within Sachem’s Cove, where this bloody episode occurred, was the summer home of landscape-design superstar, Frederick Law Olmstead, the Father of American Landscape Architecture best known for designing New York’s Central Park.

This ethereal inlet, where backyards of surrounding homes aren’t much more than slabs of gently-rounded bubble-gum hued rock, and where Olmstead spent his youthful, obviously impressionable summers, once ran red with the blood of Native Americans.

Things To Do in Guilford CT

Shot of single clamming boat in Guilford CT

DO: Segway Tour. To get the best overview of Guilford’s historic homes and shoreline, join Rich Petrillo on a delightful Segway Tour. Roll past colonial houses, diagonally through the Guilford Green (which sparks much pointing and business card-dispensing.)

Stop at the Henry Whitfield House, then out to the harbor to see sweeping views of salt marsh, Osprey nests towering above the reeds, and shore birds diving into the water like crashing kites. $70 per tour, call for tour times.

Ultra-modern condos in Colonial era town of Guilford CT

SEE: “The Spaceship.” Most of the homes in Guilford are regal and timeless; craftsman-style, Victorian, Salt Box or variations on Colonial. But near the town dock, an elliptical copper-clad structure that seems more Expo ’67 than fife and drum stands out like a shark in a Koi pond.

This unusual condo building, nicknamed “The Spaceship,” generated negative heat when first proposed nearly 35 years ago.  Now, though, Guilford has grown to embrace it.

Oldest house in CT - oldest stone house in New England - Henry Whitfield House

SEE: Guilford is best known for the 1639 Henry Whitfield Museum, the oldest home in Connecticut (and oldest stone home in New England). Built in 1639 (“the same year that the Taj Mahal was under construction,” docents like to point out), from rugged stone.

The building was both family home to Anglican Minister Whitfield and ersatz town fort.  Fires and restorations – the most ambitious one in the 1930’s – have pretty much obliterated the original interior.  But the museum still draws busloads of kids and adults who can explore the dark rooms with flashlights. $8 adults, $5 kids, May 1 – December 15, Wednesday – Sunday, 10:00 – 4:30

Eclectic clothing and hand-fused glass gallery in Guilford, CT

SIT A SPELL: Guilford Town Green. Once grazing area, graveyard and fairgrounds, the Town Green turns dense with booths at annual craft and lobster festivals. Come on an off-weekend or weekday and it’s the essence of bucolic.

Fun mix of gifts and homegoods at Mix Design Guilford CT

SHOP: The Galleries and Stores Around The Green. If you crave unusual gifts, stop into contemporary craft shop, Mix Design Store. Coolest tote for a song: a vibrantly colored Milano Bag for just $40.  Find fused glass jewelry and wearable art at glass workshop and gallery, Chroma. 

SHOP: Ella. When I’m anywhere near Guilford, I detour to shop here for well made clothing that doesn’t make me, a Baby Boomer, look like a shrink-wrapped teenybopper. Apparel is trendy and well-priced – the perfect combination.

SHOP: Breakwater BooksAny town – no matter how small – that supports an independent bookstore, is a town rich in culture, in open mindedness, and in worldly pursuits. Though not very large, Breakwater Books offers storytime for little ones, Staff Picks, special orders, and will soon be teaming up with the Guilford Marketplace next door for events and programming. Stay tuned.

Restaurants in Guilford CT

TAKE A BREAK/COFFEE: Javahut Cafe and Bistro. A local Quonset hut has been sectioned off and reimagined as a funky coffee shop, formerly Perk on Church, now Javahut Cafe and Bistro. It’s like sipping latte in an airplane hanger and tres chic.

NOSH: Hen and Heifer. Locals have embraced this petit piece of Paris in Guilford, where you’ll find macarons, madeline’s and muffins (among other French pastries) seemingly straight from France. 

EAT: Marketplace at Guilford Food Center. The Marketplace is all the rage these days in Guilford. In a former grocery store right on the Green, it’s been converted into a cool place to pick up fresh meat and fish, quench your thirst with hundreds of custom Italian Soda flavors, get the best local craft beer on tap, and grab a prepared sandwich, salad, and side for lunch with friends.  Open 7-7 Mon-Sat, 7-4 Sunday. 

Simple grilled meats, fish and veggies at The Place in Guilford CT

EAT: The Place. Beefy guys preside over a humongous flaming grill, topped with charring rib eye ($17), salmon ($14), steamed clams ($15/lb), corn ($2.75) and other local fruits of sea and field.  Owned by brothers Vaughn and Gary Knowles, The Place has made “best of” lists in national magazines and fans include celebrities like Will Ferrill and hard-to-please foodie Martha Stewart. 

Tree stump seats encircle poppy-red tables made from recycled cable spools.  Eat here frequently enough, you’ll become “stump-worthy” and garner your very own, personalized, slice of trunk. On a sunny day or Saturday night, The Place swells to 400 patrons and 22 employees. “Our worst enemy is the weather,” Vaughn admits. “Our second worst enemy is the weather forecast.” Open April – October, M-F dinner only.

Fire oven pizzas at Bufalina in Guilford CT

EAT: Bufalina. Some patrons call Bufalina’s wood-fire pizza “the best in Connecticut,” which says quite a bit since Connecticut itself is known for having the country’s best thin-crust pizza. Pros: intimate space (read – tiny), fresh food made with passion, heavenly charred-chewy crusts. Cons: paltry parking. Tues-Sat. 4:30-9pm

Ultimate porch relaxation at Bartlett Farm B&B, North Guilford CT


Hotels In Guilford CT

STAY: B&B at Bartlett Farm.  The farmhouse is right out of the Wizard of Oz, and you’ll wake up in a room much like one that Dorothy did after her twister-related bump on the head (only with luxe modern amenities).  But this farm isn’t in Tornado Ally – it’s in the northern section of Guilford CT about 7 miles from the Green and  waterfront.

On undulating farm-roads, you might whisk right by this three-room ramshackle-chic 1784 home: only a very small sign – Bartlett Farm – affixed to the red barn, gives any indication you’ve arrived.

With a veranda named by Yankee Magazine as  “The Most Relaxing Porch in New England,” and a bountiful farm breakfast that makes use of eggs from hens out back and produce picked fresh from the garden, this working farm miles from the nearest store fits the elemental definition of a “getaway.” Rooms $150 and $165 include full breakfast for 2.Guilford CT Pin

3 thoughts on “Guilford CT: Seeds of “Offbeat” Northeast”

  1. Don’t forget the excellent hiking opportunities in Guilford, which is the southern gateway for the New England Trail (“the NET”), designated one of a handful of National Scenic Trails. (It goes right past the Whitfield House and town green.)
    On clear day from Bluff Head on the trail, you can see both Long Island and the Hartford skyline.
    Visit for more hikes in Guilford and Connecticut.

  2. HI Bill- These tips are awesome. I had no idea about the NET! Now, readers (of comments) will know! Thanks for reading and commenting. Malerie

  3. Wet your whistle and have a corned beef sandwich or a six napkin burger at Augur’s Irish Pub! 29 Water Street is only steps from the historic Green!

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