In the northern region of central Connecticut, you’ll find beautiful Simsbury, which is home to scenic countryside drives, farms, historic architecture, lovely parks, hiking, and so much more. While not technically part of the famed Litchfield Hills region because it’s further east, you’ll find the same kind of vibe in town, and it’s the perfect excursion or day trip when visiting the Connecticut countryside.
This post is all about the best things to do in Simsbury, CT, and is filled with fun ideas, as well as all my personal favorite places to check out when visiting. If you’re looking to plan a little getaway to this area of the state, I have some great suggestions for you 😉
With that, let’s get started!
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Best Things To Do In Simsbury, CT
1. Stratton Brook State Park
Definitely one of my top favorite places in Simsbury is Stratton Brook State Park, which is home to 148 acres of land for all kinds of outdoor fun. Inside the park, there there different trails for nature walks and biking, a pond for swimming, and fishing along the brook is also popular here.
One of the most scenic parts of the park is the beautiful red covered bridge that hits across the brook, which adds so much character and charm to the park. One of the most notable features of the park, though, is that it was the first entirely wheelchair-accessible state park in Connecticut.
This park is also connected to the Simsbury-Farmington Canal Heritage Trail, which I’ll talk more about later in the post, which is another fantastic feature of the park.
Good To Know: This park charges an admission fee for out-of-state visitors. If there’s not a gate attendant available, look for signs in the parking area on how to pay your fee online. When I visited, my cell service wasn’t great, and I needed to take a photo of the sign and pay online when I left the park and had a stringer signal.
2. Talcott Mountain State Park & Heublein Tower
The most popular park in Simsbury is most definitely Talcott Mountain State Park, which is home to the Heublein Tower. This park is much larger than Stratton Brook, and spans over 570 acres, and has about 4 miles of trails to explore.
Most visitors come to the park to hike to Heublein Tower, which is only accessible by foot. The tower sits 1,000 feet above the Farmington Valley on a cliff, and offers incredible panoramic views from the top. This spot is especially impressive in the fall season during peak foliage. There are different hikes you can take to reach the tower, ranging between 2.3 to over 6 miles long. However, most people choose the shortest trail, which is appropriately named the Heublein Tower Trail, or the Yellow Trail on the park map.
Once you reach the tower, there’s also a museum located in the building, which is open seasonally Fridays. through Mondays during day time hours.
Good To Know: This park charges an admission fee for out-of-state visitors, so you’ll want to plan accordingly.
3. Get Some Delicious Ice Cream
In town, there are some really awesome places to get homemade ice cream, so if visiting in the warmer months, you’ll want to add these to your itinerary!
First up is Grassroots Kitchen & Creamery, which makes their own ice cream on-site in Granbury. They’re most known for having unique flavors to choose from (like goat cheese and blackberry, and rose and chocolate), but they also have all the classics. They make everything from scratch, including the jams, cookies, and cakes used in the ice cream, so every scoop here is the highest quality (and absolutely delicious!).
Tulmeadow Farm Store is another wonderful place to go, and they also make their own ice cream on-site at their farm. They always have a big list of flavors to choose from, and my favorite here is their best-seller – red raspberry chocolate chip.
Good To Know: Tulmeadow is open seasonally from April through October, and Grassroots is open year-round.
4. Visit The Simsbury Historical Society
Located in downtown Simsbury right by Grassroots (and The Coffee Spot, which is next on this list 😉), the Simsbury Historic Society is the perfect spot for history buffs. While you can view the houses from the street without heading inside, the full experience is of course worth it.
Tours on the historic buildings take place on Saturdays only, but if your plans align, this is such a great way to learn about the local history, and get up close to the town’s most historic houses. On-site, you’ll get to see 8 historic properties, as well as walk through the Ensign-Bickford Exhibition Building.
There are also gardens to see in-season, and if you happen to visit during rose season, the Wagner Rose Walk here is really beautiful.
5. The Coffee Spot
Also right downtown is the best café in Simsbury – The Coffee Spot, which is located inside an adorable pastel blue house (unfortunately, my photo above does’t do the color justice because I took this during. golden hour, but you’ll just have to trust me 😉). One of the best things about this place is that they offer some really fun seasonal drinks, and in the past have even offered coffee/latte flights, where you can sample a few different drinks. Flavored offered previously have been black forest, lavender, and maple spice. Keep an eye on their Facebook page for updates on seasonal coffee flights!
In addition to their coffee and tea menu, you’ll find awesome baked goods, breakfast sandwiches, and a sandwich menu. Throughout the warmer months, they also host mini farmers markets with local vendors, which is a really fun experience.
6. Do A Little Shopping
While I don’t consider Simsbury a big shopping destination, there are still a few cute shops that are worth checking out. And depending on where you’re coming from, they also have some more commercial shopping areas to explore, too.
The Simsbury Town Shops on Hopmeadow Street is a cool little grouping of unique shops, featuring home goods, clothing, and gifts. Fiddler’s Green is also right by The Coffee Spot with a similar vibe and a couple of shops to check out.
My favorite shops I popped into were Kindred & Crew, The Bell & Raven, and a Spoonful of Britain.
7. Drake Hill Flower Bridge
One of the more unique attractions in Simsbury, CT is the Drake Hill Flower Bridge, which was inspired by the Bridge of Flowers in Shelburne Falls in The Berkshires. Using the same concept, an old metal truss bridge that was no longer being used was transformed into a pedestrian and bike pathway, as well as a public garden space.
Every spring through fall, Drake Hill Flower Bridge is lined with flower boxes and hanging baskets with seasonal blooms, and also offers nice views of the Farmington River. It’s such a lovely and sweet little spot to enjoy during your visit, especially during flower season.
8. Rosedale Farms & Vineyards
Another one of my personal favorite things to do in Simsbury is Rosedale Farms & Vineyards. Located in the countryside, this farm offers all kinds of fun throughout the year, in addition to making their own wine, of course 😉
During their season from June through October, you can stop by to purchase their produce, flower bouquets, baked goods, and light bites from their kitchen. They also offer outdoor seating overlooking their vineyard, which is such a wonderful experience.
Rosedale does a fantastic job with season events, and here are some very cool ones to check out, depending on when you visit:
→ Sunflower Stroll through their sunflower fields – late summer
→ Corn Maze – fall season
→ Chef-to-Table farm dinners – summer and fall
→ Farm Fests – Sundays in the fall
→ Rosedale Music Series – On the weekend afternoons
9. Bike The Simsbury-Farmington Canal Heritage Trail
As part of the longest paved trail in Connecticut, the Simsbury-Farmington Canal Heritage Trail is definitely one of the most fun things to do when you visit! While the entire Canal Heritage Trail is over 80 miles long, the Simsbury-Farmington portion in this part of town is just about 5 miles one-way, making this and easy and enjoyable trail to experience.
There are a few different parking areas to pick-up the trail, but I most often use the one located downtown at 1113 Hopmeadow Street, which has a large parking lot with plenty of spaces. The trail is used for both walking and cycling, and is a great way to explore the area.
10. Flamig Farm
Known for the famous backward “EGGS” sign on their barn, Flamig Farm is a fun experience to have in Simsbury when you visit.
Open every day from April through mid-November, the farm is home to a petting zoo, hayrides, and even a very cool, farm stay experience to immerse yourself into the life of a working farm. There’s also a gift shop inside where you can purchase items with the backward “EGGS” logo to remember your trip by.
In the fall season, they also do a spooky haunted trail, which is perfect is visiting around Halloween.
11. Stop At The Pickin Patch
Another fantastic seasonal farm to visit in Simsbury is the Pickin Patch. Located right on the Avon and Simsbury border, this farm is most popular in the fall season when it’s loaded with pumpkins, cider, apples, and hosts food trailers serving up yummy apple fritters.
However, they always have fantastic produce and plants available during their entire season, including fresh fruits and veggies from their farm, potting flowers, their own jams and spreads, and local foods like honey and maple syrup.
12. Pinchot Sycamore Tree
This famous tree in Connecticut is the largest in the state, and it can be found right in Simsbury! While this isn’t a flashy attraction in the area, and doesn’t require much time, it’s actually a really cool place to visit.
This tree is at least 200 years old, but some people think it could be as old as 300 years. The trunk is measured to be around 28 feet wide, and when you stand next to it, you really get a feel for it’s size. Photos don’t do it justice.
Good To Know: There’s a small, dirt parking area by the tree, and parking is free. It’s located close to an intersection, and easy to miss, so be sure to keep an eye out as you approach.
13. Drive The Simsbury Fall Foliage Tour
The town of Simsbury made it super easy to take a scenic fall foliage drive during this magical time of the year in Connecticut, and during my most recent fall visit, I decided to check it out for myself. I’m happy to share that it was lovely, and I definitely recommend adding this to your itinerary if you visit in the fall.
While many of the roads you’ll drive on this foliage tour are the routes you’d take to get to some of the places I’ve already listed (like Rosedale Farms and the Pickin Patch), but if you’re short on time and are just looking to drive through town, it’s a great way to take in some nice foliage views.
Click here to access the directions for the Simsbury fall foliage scenic drive.
14. International Skating Center of Connecticut
A fun winter activity in Simsbury is ice skating at the International Skating Center of Connecticut, which offers public skating throughout the weekends.
The indoor rink has two ice surfaces – the NHL rink and the Olympic rink, and was even used to train Olympic medalist figure skaters Viktor Petrenko and Oksana Baiul. But you don’t have to be an expert to skate during the public skate sessions, and the rink also offers skate rentals to make your visit easy.
Good To Know: Public skate times can vary from week to week, but are usually held on Friday nights, Saturdays, and Sundays. It’s best to click here to access the current week’s skating schedule to confirm exact times, as they have to work around hockey games and such. There’s also a per-person fee for public skating, so plan accordingly.
15. Experience The Holidays With Simsbury Celebrates
If you’re looking to escape to a quaint town for a holiday getaway, Simsbury has a fun event during this time of the year called Simsbury Celebrates.
The event typically takes place the Saturday after Thanksgiving, and includes Gingerbread House Exhibit, caroling, lots of children’s activities, special performances (including The Nutcracker!), trolley rides, and ends with a fireworks show at night.
Where To Stay In Simsbury
Simsbury 1820 House: Located right in the heart of the small downtown area, this cozy spot is listed on the National Register of Historic Places, and is a great example of a traditional New England style inn. Enjoy beautiful rooms, continental breakfast, on-site dining, pool access at their sister property, and pet-friendly room options during your stay.
→ Click here to check rates & availability at the Simsbury 1820 House
The Simsbury Inn: Located just under 2 miles from the heart of downtown, this inn is also a wonderful option. The property is a bit bigger than the 1820 House, and offers an indoor pool, continental breakfast, bikes to explore town (in season), different on-site dining options, and cookies upon arrival.
→ Click here to check rates & availability at the Simsbury Inn
Fun Things To Do Near Simsbury, CT
While there are so many great things to check out while visiting Simsbury, it’s also close by to some other wonderful things to do in the area. Here’s what I recommend checking out if you have some extra time to explore nearby areas.
16. Roaring Brook Nature Preserve
Just 10 minutes from Simsbury in Canton, CT, the Roaring Brook Nature Preserve is another fantastic outdoor space to experience when you visit. Even though it’s part of the children’s museum network in the state, folks of all ages are welcomed.
At Roaring Brook, there are 5 miles of trails to explore, gardens, animal exhibits, wildlife, a turtle pond, and a scavenger hunt, which all visitors can enjoy for free during their visit.
17. Head Out On A Hike
While I’ve already mentioned quite a few parks and opportunities for hiking in Simsbury, there are so many more fantastic trails around this region of the state. Notably, I really like Peoples State Forest and the American Legion Forest, which aren’t far from Simsbury.
If you’re looking for more options, here are some great trails. to check out during your visit:
→ Turkey Vulture Ledge Trail in American Legion Forest (a short trail with really nice payoff – I really like this one!).
→ Metacomet Yellow and Orange Trail Loop
→ Jessie Gerard Trail
→ Peoples State Forest Loop
→ If you’re wanting a challenging hike, the Appalachian Trail runs through nearby Kent, and the Caleb Peak via Appalachian Trail is a good one to check out.
18. Explore Beautiful Litchfield
One of the most picturesque towns in Connecticut is Litchfield, which is about 40 minutes from Simsbury, and well worth the drive. Between the idyllic downtown and beautiful parks to see, there’s plenty to see and do to keep you busy for an entire day.
Some of my favorite things to check out in Litchfield are the White Memorial Conservation Center, Litchfield Distillery, Topsmead State Park, and Mount Tom State Park.
While in Litchfield, I also recommend making the 10-minute drive to Goshen to visit Thorncrest Farm & Milk House Chocolates. This farm is nestled into the woods, which is a unique setting for a farm, and is home to an artisanal chocolate shop. The chocolate flavors rotate frequently, but there’s always a large selection to choose from. But the best thing is, they’re absolutely delicious and worth the drive!
Psst! I have an entire guide on the best things to do in Litchfield, CT, if you need more ideas 😉
19. Plan A Day Trip To The Berkshires
Simsbury is only about an hour from the southern region of The Berkshires, so it’s very easy to explore both when in the area. While The Berkshires is a larger region, it’s also not too spread out, meaning you can definitely visit the highlights in a day trip.
The top things to do and towns I recommend seeing when visiting The Berkshires are:
→ Sheffield Covered Bridge
→ Great Barrington for a fun downtown vibe
→ Stockbridge (Naumkeag Estate and the quaint Main Street)
→ Lenox (such a charming downtown area, and I also love the trails at Pleasant Valley)
→ Pontoosuc Lake
→ If you have time to head further north, the Sheep Hill area in Williamstown is a great hiking spot
20. Elizabeth Park Conservancy In Hartford
Simsbury is only about 20 minutes from the beautiful Elizabeth Park Conservancy in Hartford, and it’s such a fun excursion to make when visiting.
The park spans for about 100 acres, and is one of the most photographed spots in Connecticut. Between the formal gardens, rose archways, open green spaces, and walking trails, it’s also one of the most impressive things to do in the area.
If you can visit when the rose arches are in bloom, I can’t recommend it enough, and it feels like a magical experience. The arch roses only bloom once per year between mid-June and mid-July, which makes it extra special to see them during that time.
However, even if you miss the rose arches, there’s still tons in bloom, and the season begins in April with daffodils and tulips, and ends in October.
Good To Know: Elizabeth Park offers free parking and admission, and had a few different large parking lots. On days where events are not taking place, parking in the lots should be easy. However, if there’s an event that day, parking becomes more difficult, and you’ll want to plan accordingly. Click here for more information about parking at the park.
21. Explore The Rest Of The Litchfield Hills
While staying in Simsbury, I also recommend taking at least a day to explore the other towns in the Litchfield Hills. I recommended Litchfield as its own suggestion because it’s the closest to Simsbury, but you can easily make a day of adding in New Milford, Washington Depot, and Kent – all of which have their own charm and character.
If you wanted to see all of them in a day, I’d recommend starting in Litchfield, driving to Thorncrest Farm, and then taking Route 7 to Kent. From Kent, continue on Route 7 south to New Milford, and then head over to Washington Depot before going back to Simsbury.
To help you plan this part of your visit, I have detailed guides on these towns, which showcase my favorite things to do.
- Things To Do In Kent, CT
- Visiting The Real Stars Hollow – Washington, CT
- Things To Do In New Milford, CT
Visiting Simsbury, CT – FAQ
Does Simsbury, CT Have A Downtown?
Yes, Simsbury, CT does have a downtown, but it’s good to know that it’s not a concentrated area with lots of shops and dining options. There are a few clusters of retail areas, but I didn’t find this to be a town centered around shopping.
However, the downtown area is home to The Coffee Spot, the Historical Society, is walkable to Canal Heritage Rail Trail, and is lined with trees and some beautiful homes, so it’s worth popping over for a bit to check out.
Simsbury is one of those rare destinations, though, where the downtown area is not its most stand-out feature.
Is Simsbury Walkable?
The downtown area of town is walkable, however, you’ll need to drive to most other attractions. Having a car is necessary while visiting Simsbury.
Best Time Of Year To Visit Simsbury, CT
This area is a fantastic fall foliage destination, and I will say that it’s worth visiting during this time to experience it. The tree-lined streets downtown are bursting with color, and you’ll also enjoy stunning foliage views while driving around the more rural parts of town.
Most of the farm stands and such are open in the fall serving up fall treats, and selling fall produce, which enhances your autumn experience.
Psst! I have a guide on Fall in Connecticut, which features my favorite fall foliage towns, things to do, and more.
What Is Simsbury, CT Known For?
Simsbury, CT is known for its fall foliage color, beautiful state parks, and historic charm.
If you’re looking to do some leaf-peeping in the fall season, Simsbury is such a great town to visit, and there’s lots of great fall foliage to admire, especially in the parks.
Is Simsbury, CT Worth Visiting?
I think so, yes! However, it’s worth noting that Simsbury’s appeal and charm lies more in its state parks and attractions, and less on its downtown and walkability. If you’re looking for a quaint downtown to visit with shops and restaurants, Simsbury has a very small version of that, and is lacking in varied options. It also has a more commercial side to it that will have chain stores.
However, Simsbury is worth visiting for the parks, hiking, and fun attractions like Rosedale Farm & Vineyards, the Drake Hill Flower Bridge, and Canal Heritage Trail (plus everything else mentioned on this list!). I’m also always impressed with the natural beauty while driving around the countryside in Simsbury.
That’s A Wrap On Things To Do In Simsbury, CT!
Now you’ve got the inside scoop on all the best things to do in charming Simsbury, CT, and I hope you’re feeling more inspired to visit. While the town is more spread out, and also home to a commercial side, it’s still filled with wonderful history, stunning parks, amazing hiking opportunities, and New England charm. Happy planning!
