13 Strange and Romantic Sites in Guilford CT: On The Connecticut Shore

WHY GO: Believe it or not, the unusual history of Guilford CT became the impetus for the Getaway Maven’s first focus on quirky destinations. Although we’ve since segued into Romantic Getaways – we’re still all about the most quirky and offbeat of romantic escapes.

Guilford CT cove

And Guilford – in New Haven County – and its neighboring shoreline towns of Madison and Clinton to the North, and Thimble Islands, an abundance of fanciful pink granite isles and outcroppings that create an otherworldly landscape, to the South, are some of the most quirkily romantic of all. (Both are perfect for short road trips). 

Guilford CT is known for its artsy boutiques, a historic town center and town green, the oldest stone house in New England, and other colonial era homes made relevant today with innovative indoor and outdoor activities. 

All this makes Guilford a low-key romantic getaway for couples who seek to be immersed in early American History, even of the macabre sort. So, let’s talk about one of Guilford’s neighborhoods, with a rather odd and bloody past.

Offbeat History of Guilford CT

Old Sachems Head Sign Guilford CT


I was touring Guilford with a town historian, as we turned into the Sachem’s Head section of town.  I’d assumed that this neighborhood was so named because it juts out into Long Island Sound – and thus, a “headland.”

But I soon learned that Sachem’s Head refers to the decapitated head of a captured Pequot Tribal Chief – the Sachem. After a territorial skirmish in 1637, Colonial Brits placed the severed head in the fork of a shorefront tree to warn other tribes of their fate should they retaliate. It’s strange that a whole neighborhood in Connecticut still bears the name of a hacked-off Native American’s head.

Sachems Cove Guilford CT

Weirdly, the 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. Most likely, the Father of American Landscape Architecture, best known for designing New York’s Central Park, had no idea of the violent history right outside his door.

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 indigenous people. 

Things to do in Guilford CT

Segway Parking Sign

DO: Read Amusements 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. Call for tour times.

Salt Cave at Healing Salt Cave and Wellness Spa Guilford CT

DO: Healing Salt Cave and Wellness Spa

Theresa Cleary, owner of the Healing Salt Cave and Wellness Spa, embraces the curative effects of halo (salt) therapy. Although the spa also offers other services, (massage, facials, infrared sauna, etc), salt initially brings people in the door. This type of treatment has been shown to reduce respiratory issues – and stress – as it did for me.

For 45 minutes, I laid back in a comfy chair, in a dark room, with “shooting stars” above, surrounded by salt: at my feet; on the walls, piped in. The Cave fosters such a stress-free environment, I quickly fell asleep. I woke up feeling refreshed and energized, ready to conquer the day, and wishing there was a salt cave in my town.

Bishops Orchards Guilford CT

PROVISION: Bishop’s Orchards Farm Market

In its sixth generation of family ownership, Bishops Orchards Farm Market has been selling its farm fresh products since 1871. Locals love Bishops for the quality of its produce, prepared foods, and a range of foodstuffs – and also for its heart – as a donor of hundreds of meals to needy neighbors. Over the years, Bishops Orchards has become so famous (having a billboard on I-95 doesn’t hurt), it’s turned into one of the highlights of a visit to Guilford CT.

Guilford Art Center CT

VISIT/SHOP: Guilford Art Center

The Guilford Art Center, hidden behind an empty office building on Church St.  just north of I-95, is composed of an art school, a gallery, and a gift shop. As a whole, it’s considered a community treasure – and a nice rainy day attraction for visitors. You’d be amazed at the quality of artwork in the gallery – some by students in the adjacent buildings. Though the school primarily caters to locals, you might be able to pop in for a one-day art workshop. Just check the website for hours, classes, and availability.

Dudley Farm Museum Guilford CT

TOUR: Dudley Farm Museum

Even if you don’t get inside the whitewashed farmhouse on the Dudley Farm Museum complex, you will want to take this self-guided tour of the collection of historical buildings on this 1845 property. Just to see what all the fuss is about.

Outbuildings on Dudley Farm Museum Guilford CT

Written with a sense of wit (e.g. –the Outhouse, “in use well into the 20th Century,” had seats for Mom and Dad, with a smaller one for kids who’d sit in terror of falling into the foul muck, most likely crawling with spiders), the online walking tour takes you to 17 stops that, besides the outhouse, also includes gardens, a sugar house, an ice house, and multiple barns.

Still a farm of sorts – there are sheep and chickens – Dudley Farm is also a Farmer’s Market location (Weds in season), and an exceedingly popular wedding venue.

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 an elliptical copper-clad structure near the town dock seems more Expo ’67 than fife and drum. It 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, apparently, Guilford has grown to accept it.

Henry Whitfield State Museum Guilford CT

VISIT: Henry Whitfield State Museum

Most communities along the Connecticut Coast have deep roots – going back to the 1600’s. And, within these communities nowadays are people who have cultivated a deep respect for the past, galvanizing a push to preserve dwellings of the earliest European settlers. 

Guilford is best known for the Henry Whitfield House, the oldest home in Connecticut. (And the oldest stone home in New England).

It was built for the Anglican Minister Henry Whitfield in 1639, “the same year that the Taj Mahal was under construction,” docents like to point out.

The sturdy stone structure was both family home to 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.

VISIT: Other Historic Homes in Guilford CT

Medad Stone Tavern Museum Guilford

Medad Stone Tavern Museum (Run by Guilford Keeping Society)

In 1803, a man named Medad Stone built his roadside establishment far from the Guilford town green, convinced that the Boston Post Road would soon be rerouted to benefit his venture. It wasn’t, so Stone never opened his tavern. In 2001, the property was bequeathed to the Guilford Keeping Society, which claims it as the “tavern that opened 200 years late.” In season, the Society runs programs and events at Medad Stone Tavern Museum. Check website for information.

Thomas Griswold House Guilford CT

Thomas Griswold Historic House Museum

The 1764 Thomas Griswold House is a perfect example of a New England Salt Box design. It remained in the Griswold Family until purchased by the Guilford Keeping Society in 1958. After two restorations – the last in 1995 – the house is now furnished in the style of the early 19th century, with several original items from the Griswold family. Programs and camps run throughout the summer season. Check website for events.

Hyland House Museum Guilford CT

Hyland House

Built in 1713, The National Registry of Historic Places describes the in-town saltbox Hyland House as a “landmark building in the history of domestic architecture.” Opened as a non-profit in 1918, Hyland House has been offering tours spotlighting US colonial history for over a century. Tours on weekends from June through September.

Guilford CT Green

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 small town.

Mix Design Store Guilford CT on the Green

SHOP: Mix Design Store

If you crave unusual gifts, stop into contemporary craft shop, Mix Design Store. It’s got the coolest stuff for home, pooch, and hard to please men. 

Breakwater Books, Guilford CT

SHOP: Breakwater Books 

Any 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 story-time for little ones, Staff Picks, and special orders.

Restaurants in Guilford CT

Marketplace at Guilford Food Center, Guilford CT

EAT: Marketplace at Guilford Food Center

A former grocery store, right on the Green, was converted into the fun Marketplace At Guilford Food Center – the place in town to pick up fresh meat and fish. Plus, 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.  

EAT/NOSH: Hen and Heifer

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

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, salmon, steamed clams, corn, 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. 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.” 

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. 

Where to Stay Near Guilford CT

Currently, there are no inns or boutique hotels in Guilford, but you will find a couple of excellent lodgings three miles up the road in Madison CT. Both The Homestead – a fun, funky and fine boutique inn, and Madison Beach Hotel – a full service lodging right on the beach – will suit your romantic inclinations just fine. 

If you’d like to explore more of the State, check out the Getaway Mavens Spellbinding Romantic Getaways in Connecticut. 

Make it a CT Shoreline Road Trip with this post that covers Guilford to Old Lyme along the Long Island Sound coast. 

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  • 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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4 thoughts on “13 Strange and Romantic Sites in Guilford CT: On The Connecticut Shore”

  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 http://www.CTwoodlands.org 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!

  4. There are lots of Air BnB and VRBO options as well. It’s great to stay in town and support local businesses.

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