This amiable coastal town in New Haven County has been on the map since 1639, and is an antiquarian’s idea of heaven.
The whole of Guilford’s town center is one Historic District, among the largest in New England.
There are more than 600 historic properties here, so a walking tour will definitely be in order.
What’s great is that five of the houses in Guilford open their doors to the public, all in the summer months.
If you need a place to start, the stone-built Henry Whitfield House (1639) is the oldest building of its kind in New England and predates the town itself by a matter of months.
1. Henry Whitfield State Museum
The oldest stone house in the region was built for one of Guilford’s founders, the English Puritan minister Reverend Henry Whitfield.
He lived here with his wife Dorothy and their nine children, but since the building had high stone walls it was also a place of refuge for the area’s early settlers.
The attached visitor center has changing exhibitions about the house and Guilford’s early European history in two galleries.
The house meanwhile has been a museum since 1904 and on a self-guided tour you explore three floors loaded with furnishings from the 17th to the 19th century.
Guides are on hand to answer questions, and out in the landscaped grounds are historic stone walls, a bronze statue of Henry Whitfield and a ship’s cannon surviving from the War of 1812.
2. Town Green
No historic New England town would be complete without a quaint old green, and Guilford has a perfect example, barely altered since the 17th century.
In just under eight acres, the Town Green is on a rectangular plot with mature trees and paved paths that run diagonally from the corners and north to south.
Allocated for grazing in the 17th century, this space was Guildford’s main cemetery until the 19th century.
A monument to look for is the Civil War memorial, hewn from pink granite and dating to 1877 and depicting a Union soldier looking towards the south.
The streetscape around the green comprises the third largest collection of historical homes in New England.
These are mostly from the 19th century, together with solemn civic buildings like the library and town hall on Park Street, and three churches on Broad Street, Whitfield Street and Park Street, all facing the green.
3. Jacobs Beach
This small but well-tended beach is as good a place as any if you want to pass a sunny afternoon doing as little as possible.
Pitching gently into Long Island Sound just beyond the mouth of the East River, Jacobs Beach is 130 metres long and comes with a lot of facilities.
You’ve got a children’s playground, a boardwalk, outdoor showers, a bath house, boat rack, picnic area, grills and courts for volleyball and basketball.
To use the beach you’ll have to pay a daily fee, whether you’re a resident or non-resident, or purchase a seasonal beach pass.
4. Hyland House Museum
One of the oldest house museums in New England, this Colonial Saltbox house went up in 1713 but is named for George Hyland, the owner-settler who bought this parcel of land in 1657. Hyland House is an exceptional state of preservation and has been a museum since 1918 after it was purchased by the Dorothy Whitfield Historic Society.
Inside there’s a wonderful cache of colonial-era artifacts and furnishings.
Among the interesting period details are the ornamentally chamfered girts, an early example of this type of decoration.
Hyland House welcomes visitors Friday to Sunday between June and September, and also opens on Wednesdays and Thursdays in July and August.
5. The Dudley Farm
The wealthy farmer and gristmill and tannery owner, Erastus Dudley, built himself this large-scale farmhouse and accompanying outbuildings in 1844. The Dudleys have a long history on this land, going back more than 300 years, and the farm’s 10 beautiful acres are managed today by the Dudley Foundation.
The Dudley Farm is frozen in the year 1900, and a tour will shine a light on life and work on a family farm in this period.
The barns and outbuildings are full of contemporaneous farming equipment and tools, and in the grounds there’s even period-specific livestock, as well as flowerbeds, herb gardens, arable fields, a farm garden, woods and meadows.
In the Munger Barn you can pore over a staggering collection of arrowheads and stone tools left behind by the Native American Quinnipiacs who were here for millennia before European settlement.
The house itself is a personal space with family quilts, tapestries and furniture.
6. Bishop’s Orchards
A big operation, this local farm has been going since 1871 and remains in Bishop family.
Depending on the season there are lots of reasons to swing by, whether you want to pick your own fruit, sample hard ciders and award-winning wines, choose from more than 20 different ice cream flavours at the creamery or buy fresh produce and homemade goodies at source from the farm stand.
Bishop’s Orchards publishes a PYO calendar on its website, telling you when its strawberries, blueberries, peaches, raspberries, pears, apples and pumpkins are ready for picking.
The winery meanwhile, was set up in 2005 and produces varietal wines from sweet to dry, from Merlot, Pinot Gris, Chardonnay, Cab Franc, Cab Sauv and Vidal Blanc.
7. Chaffinch Island Park
This scenic, lightly trafficked park is at the mouth of the West River and is an ideal place to ponder Long Island sound, walk your dog, go fishing, take picnics or go kayaking/paddleboarding.
In 22 acres there are waterside picnic tables, grills, sanitary facilities and access ramps.
From smooth pink granite outcrops you can watch the yachts drifting past and set your gaze on Falkner’s Island, while at low tide you’ll be surprised how far out you can walk.
8. Griswold House Museum
This classic Colonial Saltbox house was built around 1764 and is given its distinct profile by a lean-to at the rear.
It was constructed by Thomas Griswold III (the second generation on this land) for two of his sons, and was passed down through their descendants until it was bought by the Guilford Keeping Society in 1958. When you come, check out the rather grand entrance, flanked by fluted pilasters and capped with a pediment.
As they appear today, the interiors date from a 19th-century redesign, during the time of George and Nancy Griswold, while one room is devoted to changing exhibitions of artifacts from the Guildford Keeping Society’s collections.
Also on the property there’s a Victorian three-seat outhouse, a barn with tools and farming implements, an authentic blacksmith shop and two corn cribs.
You can generally visit on weekends from June to October, with extended opening times from Wednesday to Sunday in July and August.
9. Alder Brook Cemetery
After Guilford was settled in 1639 the main cemetery was on the Town Green, but as this was also used for grazing livestock and militia training, new spaces had to be found by the start of the 19th century.
Alder Brook Cemetery is the largest of these and dates from 1818, with many gravestones that were relocated from the Town Green.
The town has put together a self-guided tour around this peaceful and historically intriguing site, complete with audio, images and GPS coordinates for 28 of the more prestigious burials.
These include the poet Fitz-Greene Halleck (1790-1867) and the leading sociologist William Graham Sumner (1840-1910).
10. Medad Stone Tavern Museum
You can get into this Guilford Keeping Society property for tours on weekend afternoons between June and September.
The Federal-style Medad Stone Tavern (1803) has a Bates Motel kind of story: It was constructed by a local man Medad Stone, who got wind that the Boston Post Road was going to be redirected and built a tavern on the proposed route.
The route never changed, so the completed building never opened to customers and lies in a rural-residential area to the west of Guilford.
Architecturally, the Medad Stone Tavern has a gambrel roof broken by five gabled dormers, and a two-level shed-roof porch that drops down to the exposed basement level.
The building was in the hands of the Davis family, local farmers, for two centuries until was sold to the Guilford Keeping Society in 2001 and opened to the public.
Within are 14 rooms and 10 original fireplaces, and on the grounds are a barn, corn crib and expansive fields.
11. Shoreline Segways
This family-run business will show you around Guilford in a novel way, gliding on a two-wheel Segway.
Tours depart from the company’s shop at 1310 Boston Post Road and begin with a short induction process to help you learn the basics on these intuitive vehicles.
Then, depending on what you want to see, you’ll breeze off through Guilford’s Historic District and then out past the Agricultural Fairgrounds to the Town Marina.
There you can take in stirring views of Long Island Sound, Falkner’s Island, Grass Island and the tidal wetlands at the mouth of the East River.
Shoreline Segways also offers tours of nearby Hammonasset and Mystic.
12. Guilford Fair
The second oldest agricultural fair in Connecticut takes place over three days on the third weekend of September.
The event began in 1859 as a cattle show, and remains rooted in rural traditions, with events like a hotly contested horse and oxen pull, along with Connecticut’s only donkey and mule show.
The Guildford Fair also shows off lots of old-time skills, like open hearth cooking, rope-making and wool-spinning.
People across the town spend the year preparing for the fair, perfecting their photographic skills, recipes, home-grown produce and arts and crafts to enter the many competition categories.
All this fun is partnered with plenty of live entertainment and music for all the family.
13. Guilford Art Center
Set up back in 1967 to foster the town’s budding artistic talent, the Guilford Art Center is a non-profit gallery, school and shop with a busy program of workshops and events.
The Center took shape organically following the first Handcraft Expo, which took place on the Town Green in 1957. This is the largest public exhibition space between New Haven and Old Lyme, with juried and invitational exhibitions for all disciplines, which can be viewed free of charge.
The school meanwhile serves people of all ages, from pre-school to senior citizens, holding around 350 classes in anything from sketching to painting, pottery, weaving and jewellery-making.
Finally, the shop, open seven days a week, has a stunning selection of contemporary arts and crafts handmade across the country.
14. Lake Quonnipaug
North of Guildford proper but within the town limits there’s a picturesque rural lake covering 41 acres and protected by steep wooded hills.
Lake Quonnipaug is at its best in the summer when you can make the most of the 100-metre beach, swim in calm waters, rent paddleboats and kayaks, and build sandcastles.
There’s a picnic shelter just in from the shore, while the lake is popular with local fishers for its plentiful bass.
Seasonal beach passes or entrance fees for non-residents apply.
15. Falkner’s Island Lighthouse
That crescent-shaped island 3.5 miles off the coast of Guilford has had a lighthouse since 1802 to help vessels negotiate an especially dangerous portion of Long Island Sound.
The light was commissioned by president Thomas Jefferson and has the second-oldest tower for this purpose in the state.
Falkner’s Island Lighthouse is also the last functioning light station to be set on an island in Connecticut.
The island is a vital wildlife refuge, with one of the largest breeding colonies of roseate terns in the north-eastern United States.
For this reason access is prohibited during nesting season between May and August.
But there is an annual open house in September.
On this date you can normally catch a ferry from the mainland to the island’s little harbor, but there’s also a water taxi transporting people from private boats anchored west of the island to the site.