Things To Do In Simsbury CT: Top 23 Most Unique Spots | Stanton House Inn

People enjoying the afternoon sun at the Coffee Spot, occupying a historic home in Simsbury CenterSimsbury, Connecticut, is one of the most charming New England towns in the Farmington River Valley. Northwest of Hartford, the town is rich in history. Its picturesque backdrop is the Metacomet Ridge. If you enjoy woodland hiking trails, breathtaking views, and an adorable downtown, Simsbury is the perfect day trip for you.


The main attraction is Heublein Tower, a century-old monument. The ridge and the tower itself offers a breathtaking view of New England.


Simsbury’s charm and beauty have not gone unnoticed. It was named one of the top ten best places to live in America by Money magazine. Quite an achievement for a quiet little town in Connecticut, don’t you think?


Ready to explore the best things to do in Simsbury, CT? Let’s get into it:


Quick hits

  • Visit Simsbury, CT to experience the breathtaking views from Talcott Mountain State Park and the grand Heublein Tower.
  • Take a leisurely walk down memory lane at the historic Old Drake Hill Flower Bridge.
  • Enjoy the fresh air at Stratton Brook State Park and marvel at the majestic Pinchot Sycamore Tree by the Farmington River.
  • Expand your horizons by exploring other towns in the Farmington Valley. Each offers their own unique attractions!

things to do in simsbury ct map Things to Do in Simsbury CT: Top 23 Most Unique Spots
Map design by Stanton House Inn

A Brief History of Simsbury, Connecticut

Circa 1905 postcard of the interior of A. E. Lathrop's Drug Store

The town of Simsbury, Connecticut, was first known to the Wappinger people. It officially debuted as Connecticut’s 21st town in May, 1670.


Early history

In the 1600s, Simsbury was a bustling hub for the indigenous Wappinger tribe. They made their homes between the Hudson River Valley and Connecticut River. One of their bands, the Massaco, settled near the Farmington River in what is now Simsbury and Canton, CT. Europeans arrived in 1633, eager to claim new territories. They settled Windsor, Connecticut, the first Connecticut town settled. Windsor settlers saw the Massaco area as an extension of their town. They began to farm and forest the land, but didn’t establish permanent homes there.


In 1642, the General Court of the Connecticut colony decided to bestow the land around the Tunxis River, known as Mossocowe, to the inhabitants of Windsor. In 1653, Lieutenant Aaron Cook, John Bissell, and Thomas Ford received land in Massacoe from the General Court.


It was only in the following decade that settlers started to build permanent homes in the area. John Griffin, tired of Windsor’s hustle and bustle, became the first European full-time resident of Massacoe in 1663.



In 1670, three men named John Case, Joshua Holcomb, and Thomas Barber boldly requested the General Court officially recognize Massacoe as a Connecticut town. The court granted their request, dubbing the plantation “Simmsbury.” This new township included Granby and Canton, though they later separated from Simsbury. The origin of the name “Simmsbury” remains a mystery. Some speculate it pays homage to the English town of Symondsbury, where Joshua Holcomb once lived. Others believe it honors Simon Wolcott, a notable local who was often called “Sim.” The real origin, though, is long forgotten.


King Philip’s War

Postcard of Main Street in Simsbury, Connecticut, around 1912

In 1675, King Philip’s War spread rapidly across four colonies. And as a border town, Simsbury was on the precipice of danger. By August 1676, the flames of war had mostly subsided. But the embers glowed hot and dangerous until a treaty was signed in 1678.


In response to the growing threat, the Connecticut colony formed a Council of War. They implemented night watches and ensured work was done in armed groups. On October 14, 1675, the General Court ordered Simsbury’s residents to seek refuge in Windsor.


In March 1676, Simsbury was pillaged and set ablaze in the most extensive Indian War event in New England. The settlers took refuge in Windsor until the spring of 1677, when they began to return to Simsbury.


In 2015, Simsbury received a significant honor from Money magazine. It was named one of the 10 best places to live in America.


The Best Things to do in Simsbury, CT

Hiking trails through the countryside of Simsbury

Simsbury beautifully blends old-world charm with modern sensibilities. Picture-perfect parks, a rich history, and scenic bike routes are just a few things that make Simsbury special. Read on for the top attractions in Simsbury, Connecticut.


Talcott Mountain State Park

Bavarian Tower

Simsbury houses a 574-acre marvel known as Talcott Mountain State Park. This park serves as a playground for wildlife, hosting deer, foxes, and rabbits among others. The park straddles the Metacomet Ridge, a century-old fault line. The 13-mile mountain range is home to chestnut oaks, and rare plants like the pale corydalis among its native plant species. Two waterfalls defy gravity within its boundaries, and cliff-top lookouts offer heart-racing views. A highland swamp boardwalk reveals earth’s secrets, and bodies of water reflect the sky. The Blue-Blazed Metacomet Trail, a 50-mile long scar on the ridge, beckons the brave.


Heublein Tower

Interior of the tower

The Heublein Tower, a grand Bavarian-style structure, stands tall over Simsbury. You can see the tower from uphill sections of downtown. The tower offers a view that stretches across Connecticut and beyond. It was built in the 1910s by Gilbert F. Heublein, after a promise to his beloved. He promised his future wife he would build her a home here, and after making his fortune in beverages, hotels, and more, he did. Constructed out of 50 meters of steel and stone, the tower can withstand winds as fast as 100 mph. It’s perched on Talcott Mountain on the Metacomet Ridge. The tower is open from Memorial Day till the end of October, with extended hours in October to showcase Fall’s vibrant colors. You can reach the tower from the parking lot on Summit Ridge Drive, a 1.25-mile trail that has some sizable uphill stretches.


From the tower, you can see Long Island Sound, the Hartford skyline, and even Mount Monadnock, which is a distant 80 miles away in New Hampshire.


Pinchot Sycamore Tree

The largest tree in Connecticut, the Pinchot Sycamore stands proudly by the Farmington River. And it’s been doing so for at least 200 cycles of summer and winter. Named in honor of Gifford Pinchot, this tree’s impressive stats include a circumference of 23 feet 7 inches and a diameter of 106.8 inches. Nestled at the foot of Talcott Mountain, the tree reaches a staggering 30 meters towards the sky with a trunk that’s 8.5 meters around.


Old Drake Hill Flower Bridge

Drake Hill Bridge

Built in 1892, the Old Drake Hill Flower Bridge gained a new life as a footbridge in 1992. It is one of only three surviving bridges of its kind in Connecticut. The bridge spans 53 meters and has a roadway 3.7 meters wide. In 1992, a new two-lane bridge was introduced and the old bridge was adorned with wooden boxes full of colorful flowers. While not as famous as the Shelburne Falls Bridge in Massachusetts, the Flower Bridge has become an icon. It is a lovely backdrop for wedding vows and viewing spot for boat races on the Farmington River.


Simsbury Center Historic District

Simsbury Free Library in Simsbury Center

Spanning more than 70 acres and seven blocks of Hopmeadow Street is the historic district of Simsbury center. The styles of these historic buildings and homes are diverse. They range from Colonial to Early Republic, Late Victorian, and 20th-century Colonial Revival.


Major buildings that contribute to the Simsbury Center Historic District include:

  • The Simsbury Free Library, built in 1887
  • The Colonial Revival Eno Memorial Hall, erected in 1932
  • The First Church of Christ at 689 Hopmeadow St has weathered storms and sunshine since 1697
  • Located at Railroad and Station Streets, the Simsbury Railroad Depot dates back to 1875. It bears Italianate flourishes that were fashionable at the time.


The oldest property in the area is Simsbury Cemetery at 755. Established in 1688, it occupies the site of the town’s first meeting house. It’s a tranquil place on a rise of a hill, offering a lovely view of town and the Talcott Mountain beyond.


Simsbury Historical Society

The Hendrick Cottage at the Simsbury Historical Society

Occupying a modest two-acre plot, the Simsbury Historical Society comprises 16 buildings. Saunter through the gardens, or take a guided tour through the hallowed halls of the Phelps Tavern. Rotating exhibitions put Simsbury’s past on display. The Ellsworth Visitors Center, built in 1966, serves as a revolving stage for the society’s collections. Inside, you’ll find a trove of furniture, decorative arts, textiles, costumes, paintings, and relics from Simsbury’s Ensign-Bickford Company. The Visitors Center also features a play area for children, filled with old wooden toys and period costumes. The Simsbury Historical Society bridges the gap between the past and the present.


Phelps Tavern Museum

Front entrance of the Phelps Tavern Museum

The Phelps Tavern Museum is a historical gem dating back to 1711. This house and tavern was a part of the Phelps family for five generations. This historic building was named after Captain Elisha Phelps, recognized for his role in the Capture of Fort Ticonderoga in 1775. The tavern opened its doors to the public in 1786 and served patrons until 1849. In 1962, Mary Phelps Ensign Lovejoy donated it to the Simsbury Historical Society. Today, the museum offers interactive exhibits and guided tours through the period rooms. The Phelps Tavern Museum is a journey back in time to the 18th and 19th centuries when New England just was finding its footing.


Stratton Brook State Park

Stratton Brook State Park is Connecticut’s first wheelchair-accessible park, a feat it achieved over two decades ago. The park is a haven for enjoying life’s simple pleasures. You can swim in the pond, have a picnic under the towering white pines, or take a bike ride along the scenic bikeway. This bikeway was once an old railroad trackbed. The Massacoe Forest Pavilion was built by the Civilian Conservation Corps in 1935. This CT state park also offers year-round opportunities for fishing. When winter arrives, the hiking trails transform into cross-country skiing tracks. Stratton Brook State Park and its sibling, Penwood State Park, offer a day of tranquility in the great outdoors.


Rosedale Farms & Vineyards

View of the river from the Flower Bridge

This family-run establishment has been cultivating the land and reaping its rewards for over a century. Currently, the fifth generation continues the tradition, having added vineyards. They grow a variety of produce, from humble rhubarb to sweet watermelon. In the summer, Rosedale Farms & Vineyards provide fun activities like a sunflower maze and delicious pies.


But the vineyards are a sight to behold. Red grapes like Marquette and Sangiovese ripen under the sun, while whites like Chardonnay and Traminette sway gently in the breeze. As the day ends, there’s nothing quite like enjoying wine from one of the best vineyards in CT, a piece of local cheese, and a view of the setting sun. Their farm stands remain open until the last leaves of October fall.


The Storyteller’s Cottage

The Storyteller’s Cottage caters to a literary inclination. The Storyteller’s Cottage offers workshops to hone your storytelling skills. They also feature escape rooms with themes borrowed from literature.


The Cottage is housed in a vintage Victorian manor from 1896. This venue has also served as a historical CT small wedding venue, witnessing countless couples exchange vows of eternal love.


Simsbury Meadows Performing Arts Center

The Simsbury Meadows Performing Arts Center is a modern marvel where melodies and laughter fill the air throughout the year. With a capacity for 10,000 people, it’s the second-largest outdoor stage in the state. The Hartford Symphony Orchestra graces this stage in June and July during the Talcott Mountain Music Festival. But the music doesn’t stop there. From June to September, contemporary artists perform under the summer sky at Simsbury Meadows.


And during the first weekend of September, the town transforms into Septemberfest, a family event that brings everyone together for the aroma of food trucks and the sound of music. So, grab a blanket, pull up a chair, and let the music wash over you under the starlit sky at Simsbury Meadows.


Cycle Through Scenic Routes

Want to experience Simsbury in a unique way? Get on a bike and traverse through this charming town. There are numerous routes, showcasing the picturesque landscapes and quaint neighborhoods that make Simsbury a Connecticut gem. Don’t own a bike? No worries. The Bicycle Cellar offers rentals, and there’s also a town bike share program.


Farmington Canal Heritage Trail

Take a journey along the Farmington Canal Heritage Trail. This 14-mile stretch is perfect for a leisurely stroll or a brisk bike ride. Once the longest canal in New England, this path offers a glimpse into the region’s storied past. If you’re lucky, you might spot some local wildlife. And if you’re unlucky, you might have a run-in with a bear, as we did in nearby Farmington, Connecticut. But it’s still an ideal escape from the hustle and bustle.


Flamig Farm

Flamig Farm is a place where joy can be found in the simplest of things, regardless of age.

  • They have a petting zoo, hosting horses, pigs, and other animals.
  • Pony rides will make you feel like a western movie cowboy.
  • Flamig Farm also host seasonal activities. In the fall, when the leaves turn orange and the air is filled with the scent of pumpkin spice, you can enjoy a spooky hayride. And in the winter, when the world is covered in a blanket of white, you can visit Santa himself.


With a certain rustic charm, Flamig Farm is a must-visit spot in Simsbury, especially for families. It also hosts one of the best bed and breakfast farm stays in all Connecticut.


Roaring Brook Nature Center

Located in nearby Canton, Connecticut, Roaring Brook Nature Center is a haven for nature lovers. Established in 1948, the center is a living encyclopedia of the natural world. It offers exhibits that showcase wildlife and the environment, and houses a variety of animal species. Guided walks provide an invigorating and educational experience. The center is a home to a diverse range of creatures, from snakes and turtles to frogs and salamanders. It also features a small zoo and gardens teeming with wildflowers, butterflies, and birds. The center takes care of Werner’s Woods, a five-mile wilderness area. You can buy trail maps and wildlife checklists at the center’s store to explore further. The center also hosts “Discovery Days” for students, seasonal guided walks, summer concerts, and a whimsical Halloween “Hobgoblin Fair”.


International Skating Center

A world-class facility in Simsbury is how you’d describe the International Skating Center of Connecticut. It boasts two ice rinks, a weight training room, and a ballet studio for comprehensive skater training. The International Skating Center also houses the J.A.M. Pro Shop for your gear needs. And Sk8ters Cafe is a full-service restaurant with rink-side dining.


Restaurants in Simsbury, CT

Alcohol at one of the best restaurants in Simsbury, Connecticut

Simsbury’s dining scene is more diverse than you’d expect, from its size. This town is home to a variety of restaurants that will surely satisfy your taste buds. Soma Grill, for instance, is a fusion of American and Mediterranean flavors, offering a diverse and delicious menu.


Another must-try is Millwright’s Restaurant, where farm-fresh American fine dining is served in a room with a breathtaking waterfall view. For a more casual dining experience, they also have a tavern.


Antonio’s Restaurant is a cozy, family-friendly pub filled with fascinating knickknacks. It serves comforting American & Italian fare.


If you’re craving for Chinese dishes with a hint of traditional Thai specialties, head over to Table 570 Asian Fusion. And don’t miss Abigail’s Grille and Wine Bar. It’s a Colonial-era tavern serving contemporary American cuisine. You can enjoy their offerings on the patio or in the cozy dining room.


Hotels, Inns, and Places to Stay in Simsbury, Connecticut

Simsbury 1820 House

Simsbury, Connecticut, is an excellent destination for a day trip in CT. However, if you’re captivated by the area’s charm and wish to explore more, there are numerous cozy Connecticut bed and breakfasts for overnight stays. With its charm and grace, Simsbury is a top choice for those seeking weekend adventures in Connecticut.


Simsbury 1820 House

Step into the Simsbury 1820 House, where history and comfort coexist. This charming inn offers 31 rooms. Each one is a testament to a bygone era, furnished with antiques that echo tales of yesteryears. Despite its historical charm, modern comforts are not forgotten. Free Wi-Fi and private bathrooms offer a sanctuary of solitude.


Start your day with a delightful continental breakfast, akin to a sunrise over the Connecticut River. After a day of exploring Simsbury, retreat to your room. Let the lullaby of room service send you off to dreamland.


The Simsbury 1820 House is more than just a place to rest. It’s a taste of history, a slice of luxury, and a haven to return to after a day of adventures.


The Simsbury Inn

The Simsbury Inn stands as a beacon of rest and relaxation. This elegant hotel offers snug guest rooms decked out with modern conveniences. These include free Wi-Fi, a coffeemaker, an iron and board, a mini fridge, and plush beds. The hotel also features an indoor heated pool and a Jacuzzi for your enjoyment. For those who want to stay fit during their stay, a health club is available. When hunger strikes, you can choose from several on-site dining options. The Simsbury Inn, with its warm atmosphere and attentive service, ensures a memorable stay in Simsbury.


Directions to Simsbury, CT, from Greenwich, CT

First Church of Christ in Simsbury Center

Are you planning a journey from Greenwich, CT to Simsbury? Get ready for a 90-mile drive that will take about an hour and a half if you choose the scenic route via I-95 N and CT Route 8.


If you prefer public transportation, you can take a train from Greenwich to Hartford Amtrak Station. From there, a bus or taxi can take you to Simsbury.


Either way, Simsbury will welcome you with its charming attractions and natural beauty.


More Towns and Cities to Explore Near Simsbury, Connecticut

View of Avon from the Metacomet Ridge

If you’re eager to explore more, consider visiting some of the towns and cities near Simsbury. Each of these places offers unique attractions and experiences in Connecticut. You can discover history in museums, shop in bustling centers, or relax in beautiful parks. By venturing into these neighboring territories, you can enrich your Connecticut adventures. So, why not extend your journey? Dive deeper into the region’s rich culture and history. Remember, life is an adventure waiting to be experienced.


Avon, CT

The Pickin' Patch in Avon, CT

Just a short distance from Simsbury, you’ll find Avon, CT. This charming place offers a variety of attractions:


  • The Farmington Valley Arts Center
  • Talcott Mountain State Park
  • The Pine Grove Schoolhouse
  • The Buckingham Road Recreation Area and the Fisher Meadows Recreation Area


With its stunning beauty and rich culture, Avon is an ideal destination for a CT day trip or a weekend getaway.


West Hartford, Connecticut

Elizabeth Park Rose Garden in West Hartford

West Hartford, Connecticut, is a lively town with a lot to offer. The Elizabeth Park Rose Garden, a stunning spectacle of nature’s artistry, is a must-see. Blue Back Square is the center of town. The Noah Webster House is a local historical site. With its blend of historical tales and modern conveniences, West Hartford is a must-visit spot on your weekend trips in Connecticut itinerary.


Wethersfield, CT

Old Village Wethersfield, CT

Wethersfield, CT, proudly wears its history. This town is rich with historic sites that echo the tales of the past. If you’re interested in history, Wethersfield is the place to be. It features Historic Wethersfield and the Old Wethersfield, both boasting numerous colonial buildings.


The town’s historical significance is also reflected in the Flag of Connecticut. One of the three grapevines on the flag represents Wethersfield, acknowledging the town’s role in the state’s history. So, if you’re looking for a trip back in time, Wethersfield should be on your list.


Hartford, Connecticut

Downtown Hartford

Hartford, Connecticut, is a place with a multitude of activities to keep you interested. The Mark Twain House & Museum is a must-visit, where the spirit of literature’s wittiest man still lingers. The Wadsworth Atheneum Museum of Art is sure to captivate your senses. Then there’s Dunkin’ Park, where the crack of a bat is a sweet sound to any baseball fan’s ears.



Walking along the main street of Simsbury is a delight

Curious about Simsbury, Connecticut? This New England gem is steeped in history and filled with natural beauty. It offers a variety of activities capable of entertaining even the most adventurous souls. Whether you’re drawn to the allure of Talcott Mountain State Park, the architectural grandeur of the Heublein Tower, or the culinary delights of Soma Grill, Simsbury has something for everyone.


Frequently Asked Questions


What is Simsbury CT known for?

Simsbury, Connecticut, is a historical town. Echoes of the Revolutionary War can be found in New-Gate Prison, and the town was once home to the nation’s first steel mill, carpet factory, and safety fuse company. These beginnings led to its growth into an aerospace and manufacturing hub. Simsbury also boasts natural beauty with the Farmington River and Heublein Tower, and cultural attractions like the Simsbury Meadows Performing Arts Center and the Simsbury Historical Society.


Is Simsbury CT a wealthy town?

Simsbury, Connecticut, is a prosperous town. It boasts a median household income of $134,688. With a population of 24,517 residents, it ranks as the 13th wealthiest town in Connecticut. Quite impressive for a quaint New England town!


Does Simsbury CT have a downtown?

Indeed, Simsbury CT has a lively downtown. This area is a vibrant blend of history and entertainment, where the past is as lively as a three-ring circus. Additionally, it offers a variety of eateries, each serving up unique culinary experiences.


Is Simsbury CT a nice town?

Well, my dear reader, Simsbury is a veritable utopia. It boasts grand schools that offer top-notch education. Historic landmarks stand proud, narrating tales of yore. The town bustles with shops and restaurants, representing a vibrant present. With a balance of respect for history and a vision for growth, Simsbury promises an extraordinary future. It’s more than a nice town, it’s exceptional.


What are some popular attractions in Simsbury, CT?

Simsbury, CT, my friend, is a town that’s brimming with charisma! The towering majesty of the Heublein Tower and the age-old wisdom of the Pinchot Sycamore Tree are just some of its attractions. Talcott Mountain State Park, a 574-acre haven for wildlife, invites you to venture into its wild heart. Alternatively, Stratton Brook State Park offers a tranquil escape from the hustle and bustle of everyday life.


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