Connecticut has a reputation for wealth and pretension.
And while you can find that, if that’s what you’re into, that’s not all you’ll find here.
In fact, in this Connecticutians mind, there is much that is unique, quirky, quaint, and charming about the state.
Take Danbury, Connecticut. Many of the best things to do in Danbury, CT, are wonderfully unique.
Tucked away from the Connecticut shoreline yet still part of Fairfield County, Danbury is close to Litchfield County. It and the surrounding towns have more of a relaxed, middle class feel than some other parts of the state.
Located about 55-miles northeast of New York City, Danbury is about an hour drive from downtown Greenwich, Connecticut. If you’re up for a New England road trip this is a must on your list of stops, especially on fall foliage driving routes.
A brief history of Danbury, Connecticut
European settlers from Stamford and Norwalk, Connecticut, settled in the Danbury area in the late 1600s.
For some reason, they decided that “Swampfield” was a better name than the one given by local tribes, Pahquioque.
They changed their mind two years later and named their town after one in England.
Danbury was a major supplier of munitions to the Continental Army during the Revolutionary War. So much so that the British raided and burned the town to the ground.
Danbury’s Heyday
After the War of Independence, Danbury’s hat making business exploded from a small, handmade operation, into a major industry.
Thanks to that 150 years or so of hatmaking, Danbury still retains the name of “Hat City”.
Unfortunately, downtown Danbury never recovered from:
- The decline of hat manufacturing (and hats going out of style)
- The post-World War II exodus of city inhabitants to the surrounding towns
- A serious flooding disaster in the mid-1900s
And yet, that decline saved much of the area from the rampant development you see along the Connecticut shoreline.
You don’t have to go far to find bucolic settings, both in Danbury and the surrounding towns.
Ready to plan a CT day trip? Then read on for the 15 most unique things to do in Danbury, CT.
15 of the most unique things to do in Danbury, Connecticut
Like much of the state, most travelers only pass through Danbury to avoid the traffic on the coast on their way to or from Boston and New York City.
And yet, an hour or two poking around town and nearby is well worth the effort.
Outdoor activities in Danbury, CT
From hiking to history, outdoor enthusiasts will delight in this corner of the state.
Glacial Erratics at Ives Trail & Greenway
Danbury named the Ives Trail & Greenway after native modernist American composer, Charles Ives.
This 20-mile trail in the Housatonic Valley connects Danbury to nearby Ridgefield, Bethel, and Redding.
The first legs of the journey are all you need to spot glacial erratics. These are impressive boulders that have sat sentient since the end of the last ice age.
2) Sybil Ludington Statue
Celebrate girl power with a salute to this bronze statue depicting the nighttime ride of Sybil Ludington.
When a messenger brought word that British troops were attaching Danbury, Sibyl volunteered to ride. Despite being only 16 years old, she rode through the night to rally militiamen working on their farms.
She rode close to forty miles over the night of April 26, 1777, to rally the militia to respond.
Though they arrive too late to stop the British, they managed to harry the troops as they departed.
And thanks to the warning, there were far fewer casualties than there could have been.
Ms Ludington’s statue sits outside of the Danbury Public Library.
3) Hat Maker Statue
This statue commemorates Zadoc Benedict. This Danbury native discovered a felt-making process matting animal furs together. As a result of his business, Danbury became the “Hat City of the World”, a title they wore proudly for almost a century.
Quaint and quirky, this statue on the grounds of City Hall is emblematic of Danbury.
4) Balanced Rock of North Salem, New York
Along the old stagecoach road to Danbury, just over the border from Danbury, sits an attraction that inspires debate. Take a selfie at the balanced rock, an attraction that has people at odds whether it is some sort of Druid altar or a glacial erratic.
You decide!
Spoiler alert, few people actually believe this rock in the town of North Salem, NY, is the work of Druids.
But what’s a road trip in Connecticut without a bit of whimsy?
5) Candlewood Lake
This is the largest lake in Connecticut. Formed by a hydroelectric dam in the 1920s, it spans over 5,400 acres in pristine, majestic surroundings.
This is the place to go for outdoor activities like boat rentals, water sports, and fishing.
With so many vacation homes clustered around it, Candlewood Lake has some of the area’s priciest real estate. It’s also the site of the idyllic Squantz Pond State Park.
6) Richter Park Golf Course
If you feel outdoor activities in Danbury CT must include a round of golf, many view the Richter Park Golf Course as the best public course in the Tri-State area.
Before turning your nose up at the public idea, this public golf course features stunning undulating fairways sitting snug against the shores of the West Lake Reservoir.
Designed by Edward Ryder, be prepared to tame your swing if you want to miss one of the 14 water hazards on this 18 hole course.
7) Ives Concert Park
Music lovers appreciate the name of this pond-side park, honoring Modernist composer Charles Ives (1874-1954). A native to the city, his name holds strong cultural ties to the site known for its impressive summer program of both concerts and theatre performances.
Check the website for Ives Concert Park for upcoming concerts.
8) Danbury Parks
The hills of the area connect a series of stunning parks from the Hemlock Hills in the west and span east through Pine Mountain, Bennett’s Pond State Park and the Wooster Mountain State Park Scenic Preserve.
Nature’s most impressive work features peaks rising over 300 meters and landscapes dense with trees. Some of the best hiking trails in Connecticut are a short drive from Danbury.
The lovely southern foothills of the Berkshire Mountains extend from western Connecticut, through Massachusetts and into Vermont. Here, some of the most breathtaking hiking trails lead to stunning vistas.
If Danbury’s parks aren’t sufficient for your outdoorsy spirit, continue driving north into the Litchfield Hills and the Connecticut Berkshires. Some of the parks up this way, like the Flanders Nature Center, are on the list of the best free things to do in Connecticut.
9) Blue Jay Orchards
If you’re looking to indulge a sweet tooth, a stop at this 140-acre orchard is a must. In fact, this apple orchard made the list of the best places for apple picking in all of Connecticut.
Depending on the time of year you can pick apples and then pack your car with an assortment of their market’s sweet treats.
Rumor has it people travel miles just to enjoy just one of their famous apple cider donuts.
10) Collis P. Huntington State Park
This expansive park features 1,000 acres donated by the heirs of 19th-century railroad magnate Collis Potter Huntington.
Here, you’ll find a beautifully landscaped property, man made ponds, and a delightful stone lighthouse.
Sculptures of bears and wolves by Anna Hyatt Huntington (1876-1973) are some of the most remarkable points at the entrance to Collis P Huntington State Park.
11) Elephant’s Trunk Flea Market
Without question, the best of the Connecticut flea markets is also the largest in New England.
At least, that’s what Elephant’s Trunk Flea Market claims.
Open almost all year on Sunday mornings and early afternoons, this outdoor flea market gained extra fame from the show, Flea Market Flip.
You never know what you’ll find at this market in an agrarian section of New Milford on Route 7.
12) Tarrywile Park
We’ll end this section on a grand note. Tarrywile Park’s 722 acres makes it the largest municipally-owned town Park in the State of Connecticut.
Not only will you witness some of the most awe-inspiring scenery, but the park offers access to 21 miles of hiking trails to take in the views.
However, the natural features compete with the majesty of the Tarrywile Mansion, and neighboring Hearthstone Castle. Listed on the National Register for Historic Preservation, the mansion now acts as the community center for the City of Danbury.
Stroll through the formal gardens, former dairy farm, and orchard and enjoy the bucolic appeal of the park.
Hearthstone Castle
Head into the hills for the romantic ruins of one of the most unique attractions in Connecticut.
New York photographer E. Starr Sanford built the medieval-inspired castle in 1899 as a summer retreat. The home’s unique façade features local stone, with a barely intact veranda built from imported Italian wood. The castle featured nine bedrooms, a library, and a billiard room.
The castle changed hands a few times, with the Parks family taking over in 1918. They owned the home for 70 years, naming it Hearthstone after the castle’s eight fireplaces. Despite its current sorry state, the abandoned castle strikes an imposing figure ensconced in the woods.
The city plans to create a garden within its walls, completion date to be determined.
Indoor things to do in Danbury, Connecticut
As is the case with much of the state, there are plenty of Connecticut museums and indoor activities to enjoy, regardless of the weather.
13) Danbury Railway Museum
Built in 1903, downtown Danbury’s train station is now a fully restored museum.
Even if you aren’t crazy about trains, a love and appreciation of the Northeast’s rich past are all you need to find this stop fascinating. You’ll discover a collection of historically significant artifacts and an extensive rail yard with historic railroad equipment and rolling stock.
But what makes the Danbury Railway Museum a must is a chance to take a weekend ride on a historic Connecticut train.
14) Demon Murder Trial Sites
Fan of the macabre or all things satanic?
Or perhaps you’re a lawyer fascinated by clever defenses?
Either way, one of the most unique things to do in Brookfield CT is to visit the site of the infamous case of 19-year-old Arne Johnson. He was tried at the Old Court House for murder, where lawyer Martin Minella entered a plea of not guilty by reason of demon possession.
The judge threw out the defense, forcing the lawyer to fall back on a more conventional self-defense argument.
Still, it remains the only case in which a demon was blamed in a court of law for a defendant’s actions.
Since nothing fantastical actually happened at the courthouse, this isn’t on the list of the most haunted places in Connecticut.
Still, it’s historically interesting.
15) Danbury Museum & Historical Society
Road trips don’t make the list of the best places to road trip from NYC without a few historic stops.
You can do it all in one stop at this museum consisting of five historic buildings.
The Danbury Museum & Historical Society started to save the John Rider home, constructed in 1785, from becoming the site of a gas station.
The other four buildings that the Historical Society maintains include:
- Huntington Hall
- John Dodd Hat Shop
- Little Red Schoolhouse
- The studio of famous opera singer Marian Anderson
If it’s raining and you need indoor things to do in Danbury CT this stop fits the bill.
Wineries and breweries near Danbury
Fewer developers also means more space for breweries and wineries in the area! While wineries are usually a daytime activity, breweries are high on the list of things to do in Danbury, CT, at night.
Some great Connecticut breweries near Danbury include:
- Nod Hill Brewery
- Redding Beer Company
- OEC Brewing
And to sip a glass of wine surrounded by bucolic scenery, your picks for fantastic Connecticut wineries near to Danbury are:
- White Silo Farm and Winery
- DiGrazia Vineyards and Winery
- Hopkins Vineyard
Places to Eat & Restaurants in Danbury, Connecticut
As far as Fairfield County goes, Danbury has some of the most inexpensive real estate in the county.
And that makes it an ideal destination for recent arrivals to America, who bring their fantastic culinary traditions with them.
Danbury and nearby towns host some fantastic international cuisines, including:
- Middle Eastern, like Kibberia
- Vietnamese, like Pho Vietnam
- Lebanese, like Nour Lebanese Cuisine
Head down to nearby Ridgefield, CT, for two of the most romantic restaurants in Connecticut. You’ll also find a solid option for barbeque in a state that’s not Southern, Hoodoo Brown Barbecue.
Breakfast in Danbury, CT
Running a Connecticut bed and breakfast, we know a thing or two about breakfast. And this writer is a fan of diners, as any good New Englander is.
And Danbury is a bit of a time capsule for nostalgic diners. Some of the most popular are Holiday Diner, Sonny Side Up, and Elmer’s Diner.
Hotels, Inns, and Places to Stay in Danbury, Connecticut
Danbury, Connecticut, about a 50-minute drive from Greenwich, CT, via I-684 North through Westchester County, NY. It takes a bit longer if you take the Merritt Parkway to Route 7 in Norwalk and head north from there.
Both are rather scenic, once you get away from the coast. Though the highway obviously has fewer stoplights.
So Danbury makes a great Connecticut day trip from Greenwich.
But if you’d like to stretch your visit out, there are plenty of places to stay in and around Danbury.
Bed and breakfasts near Danbury, CT
Chain hotels dominate the city center of Danbury. So, if you’re looking for a little quaint charm up this way, you’ll have to head towards some of the more bucolic surrounding towns:
West Lane Inn
The historic district of Ridgefield, CT, is one of New England’s most picturesque colonial towns. Grand historic mansions line the main street of Ridgefield, leading to the charming cluster of downtown. And the West Lane Inn is just around the corner from Main Street, close to the Fountain. Built in 1849, West Lane Inn combines the charm of a small country inn with all of the amenities of a hotel.
Evergreen Inn
Southbury, Connecticut, hosts the Evergreen Inn. This 200-year-old Federalist-style home has six guest rooms and shared spaces. Brian and Jennifer Cascone bought it in 2017. They redesigned the interior to highlight the original architecture and flooring. The innkeepers once owned a catering business and have a love for good food. Jennifer creates homemade breakfasts from scratch each morning. The Evergreen Inn offers a stone and gunite pool, set amongst a lush garden, and offers a variety of cocktails to create.
Homestead Inn
New Milford is a charming town in Connecticut’s beautiful Housatonic Valley, the start of New England. According to New Milford, anyway. And the historic Homestead Inn is on the north end of the town’s Village Green. The inn, built in 1853, has been hosting guests since 1928. It’s the perfect base to explore Litchfield County.
Hotels in Danbury, Connecticut
You’ll find all the major chain hotels in Danbury: Holiday Inn Express, SpringHill Suites by Marriott, Hampton Inn, and Hilton Garden Inn, to name a few. If you’re looking for something a little more local, a few options here are:
Ethan Allen Hotel
If the name sounds familiar, it’s because of a certain famous New Englander, and the furniture company named in his honor. The Ethan Allen Hotel has 193 beautiful guest rooms and suites. Each room has a separate living area and bedroom, with classic Ethan Allen decor. You’ll also find pet-friendly hotel rooms here. If you don’t feel like leaving once you’re here, the hotel hosts a restaurant and bar. Additional amenities here include a seasonal outdoor pool, exercise room, and business center.
Hotel Zero Degrees Danbury
Hotel Zero Degrees opened in 2016. The hotel, like brand flagship Delamar Greenwich Harbor, has modern, stylish décor and an eco-friendly vibe. The lobby has plenty of seating, tables, outlets, and a fireplace, as well as natural lighting and access to outdoor green space. The hotel has woods, a fire pit, and an outdoor bar, and the rooms and lobby overlook woods on one side. The 114 comfortable rooms are designed with electronic needs in mind, with plenty of workspace and living space. The walk-in showers are popular. Breakfast is served for free in an open dining room with views of the outdoor firepit lounge. Terra, the onsite restaurant, offers a variety of spirits, friendly bartenders, and beautiful views. If the name is familiar, it’s because it’s a spin-off of one of the most popular restaurants on Greenwich Avenue.
Both of these options are also two of the most pet-friendly hotels in Danbury, CT, by the way.
Even more things to do in Connecticut
Once you’ve finished this list, keep exploring the nearby towns, many of which are some of the most charming in Connecticut:
- Ridgefield
- New Milford
Or continue into Litchfield County for even more quaint towns and outdoor activities. Danbury is a perfect starting point for exploring romantic places in Connecticut.
If you’d rather head to another part of the state, some more cute towns to explore include:
- Westport, CT
If you’re planning a fall visit to Danbury and the Litchfield Hills, be sure to explore our guide to Fall in Connecticut.
Though really any time of year is great for exploring the area. Be sure to check-out:
- The guide to springtime activities across Connecticut, including Danbury
- Or what to do near Danbury on our list of winter activities across CT
- And summertime largely plans itself, but feel free to read our guide to summer in CT, just in case
Inside knowledge of the lesser-known attractions is what makes a trip to Connecticut special.
Be sure to read our guide to the most unique and quirky attractions in Connecticut, and be sure to download a free copy of the Connecticut Travel Guide.
Updated and republished: August 25, 2023
