15 Best Things to Do in Guilford (CT)

Written by Veronique Raes
Updated on
Our travel recommendations are based on our personal experiences and research, written by locals and travel experts with deep familiarity with the destination. When you book a hotel or tour that we link to, we may earn a commission.

This amiable seaside 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 enormous Historic District, among the largest in New England. There are more than 600 historic properties here, so I think 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. It even predates the town itself by a matter of months.

1. Henry Whitfield State Museum

Henry Whitfield State MuseumSource: LEE SNIDER PHOTO IMAGES / shutterstock
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. Since the building had high stone walls it was also a place of refuge for the area’s early colonial 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. On a self-guided tour you explore three floors loaded with furnishings from the 17th to the 19th century.

I was pleased with the docents, who are on hand to answer questions. 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

Town GreenSource: Dougtone / Flickr | CC BY-SA
Town Green

No historic New England town would be complete without a quaint old green, and Guilford has a perfect example. This space has barely changed 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 it depicts a Union soldier looking symbolically towards the south.

I recommend exploring the townscape around the green. This comprises the third largest collection of historical homes in New England.

These residences date from the 19th century, and are matched with solemn civic buildings like the library and town hall on Park Street. There are three churches on Broad Street, Whitfield Street and Park Street, all fronting the green.

The oldest of these is the Federal-style Congregational Church (1829), on the north side.

3. Jacobs Beach

Jacobs BeachSource: goodstreetsorg / Flickr | CC BY
Jacobs Beach

This small but well-tended beach is as good a place as any if you want to spend 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 420+ feet long and comes with a lot of amenities.

I saw a children’s playground, a boardwalk, outdoor showers, a bath house, boat rack, picnic area, and grills. There are also simple sports amenities, with 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. Seasonal beach passes are also available.

4. Hyland House Museum

Hyland House MuseumSource: Versageek / Wikimedia | CC BY-SA 3.0
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. He was the owner-settler who bought this parcel of land in 1657. 

Hyland House is in 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 for guided tours on weekends, June through September. I’d also keep an eye out for demonstrations of old-time skills, like blacksmithing.

5. The Dudley Farm

Dudley FarmSource: goodstreetsorg / Flickr | CC BY
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 as it was in the year 1900, and a tour will shine a light on life and work on a family farm in this period. The house’s homey interior felt personal to me, and is filled with family items like quilts, tapestries and furniture.

The barns and outbuildings are full of contemporaneous farming equipment and tools. Out on 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.

6. Bishop’s Orchards

Bishop's OrchardsSource: goodstreetsorg / Flickr | CC BY
Bishop’s Orchards

A big operation, this local farm has been going since 1871 and remains in the Bishop family.

Depending on the season, I can think of lots of reasons to swing by Bishop’s Orchards. You can pick your own fruit, sample hard ciders and award-winning wines, and choose from more than 20 different ice cream flavors at the creamery. 

There’s also a bounty of fresh produce and homemade goodies at source from the farm stand.

Bishop’s Orchards publishes a useful PYO calendar on its website. As annual conditions fluctuate, it will tell you when the 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. Among them are Merlot, Pinot Gris, Chardonnay, Cab Franc, Cab Sauv and Vidal Blanc.

7. Chaffinch Island Park

Chaffinch Island ParkSource: Elizabeth Stegina / shutterstock
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. You can walk your dog, go fishing, browse the beach for shells, take picnics, or go kayaking/paddleboarding.

In 22 acres there are waterside picnic tables, grills, sanitary facilities and access ramps.

I can’t get enough of the views from the smooth pink granite outcrops. Here you can watch the yachts drifting past and set your gaze on Falkner’s Island. Then at low tide I was surprised at just how far out I could walk.

8. Griswold House Museum

Griswold House MuseumSource: Versageek / wikipedia
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. The property 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. Meanwhile 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

Alder Brook CemeterySource: alderbrookcemetery.com
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. I was interested to see that many gravestones were relocated from the Town Green.

The town has put together a self-guided tour around this peaceful and historically intriguing site. Found online, it’s 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

Medad Stone Tavern MuseumSource: Magicpiano / wikipedia | CC0
Medad Stone Tavern Museum

You can get into this Guilford Keeping Society property for tours on weekend afternoons between June and September. You can also attend open houses, or arrange a visit by appointment. 

The Federal-style Medad Stone Tavern (1803) has a story that reminded me of the Bates Motel. 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. Then it 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. GreenStage Guilford

Previously known as the Guilford Performing Arts Festival, this event is a blast of culture at the end of summer. Across three days, GreenStage Guilford brings some two-dozen performances.

Based on and around the Town Green, you’ve got live music, drama, dance, and spoken word. It’s a great opportunity to catch new work, every year there’s always a few worldwide premieres. 

GreenStage Guilford is about more than spectating. When I came you could take part in a host of workshops and master-classes, all with a performance theme.

12. Guilford Fair

Guilford FairSource: Aldon / Flickr | CC BY-SA
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 I appreciate how it’s still rooted in rural traditions. Among the events when I came were hotly contested horse and oxen pulls, 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, carnival rides and music for all the family.

13. Guilford Art Center

PaintingSource: Syda Productions / shutterstock

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 preschool to senior citizens. In fact, there are around 350 classes annually, in anything from sketching to painting, pottery, weaving and jewelry-making.

Finally, the shop is local go-to for me. It’s open seven days a week, and stocks a fine selection of contemporary arts and crafts, handmade across the country.

14. Lake Quonnipaug

Lake QuonnipaugSource: Douglas. P. Olsen / Wikimedia | CC0
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.

From my experience, Lake Quonnipaug is at its best in the summer. At this time of year you can make the most of the 330-foot beach, swim in calm waters, rent paddleboards 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 apply, and there are entrance fees for non-residents.

15. Falkner’s Island Lighthouse

Falkner's Island LighthouseSource: Allan Wood Photography / shutterstock
Falkner’s Island Lighthouse

That crescent-shaped island 3.5 miles off the coast of Guilford has had a lighthouse since 1802. Falkner’s Island Lighthouse was erected to help vessels negotiate an especially dangerous patch 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 Northeastern 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. There’s also a water taxi transporting people from private boats anchored west of the island to the site.

15 Best Things to Do in Guilford (CT):

  • Henry Whitfield State Museum
  • Town Green
  • Jacobs Beach
  • Hyland House Museum
  • The Dudley Farm
  • Bishop's Orchards
  • Chaffinch Island Park
  • Griswold House Museum
  • Alder Brook Cemetery
  • Medad Stone Tavern Museum
  • GreenStage Guilford
  • Guilford Fair
  • Guilford Art Center
  • Lake Quonnipaug
  • Falkner's Island Lighthouse