Top 23 Things to Do in Simsbury, CT; Farms, Food, Hikes, More!
Tucked within the northern chunk of the Farmington Valley, Simsbury, Connecticut is a quaint and happening little town rich with history, tons of natural beauty, great food, and a vibrant local culture with so much to see and do.
In this post, we cover 23 things to do right here in Simsbury - you don't to have go far for a perfectly fun and adventurous day! With so many scenic farms, amazing places to eat, venues to catch a live band, hike a trail with epic views, explore a historic tower, or just drive around capturing pretty pictures - your day can be as full as you want it to be!
Living right next door in Avon, I head to Simsbury at least once a week for either a walk with the dogs at one of our favorite parks or farm trails, a baked good and coffee from one of the numerous cafes, or produce from a local farm store. You can trust me when I say this article delivers the BEST things to do in Simsbury - because I live here and do them all the time!
First let’s explore the fascinating history of Simsbury and then we'll dive into 23 awesome things to do in this special town.
A Glimpse into Simsbury’s Past
Simsbury’s story begins in 1670 when it was incorporated as a town, making it one of the oldest in Connecticut! One of many interesting colonial facts about Simsbury is its connection to the infamous Nathaniel Bacon’s Rebellion. In 1676, during King Philip’s War, the town was hastily abandoned, and settlers sought refuge in Windsor.
Native American warriors then burned much of Simsbury to the ground and they then took in the smoldering view from Hatchet Hill. The resilient townsfolk were not deterred by this tragic and violent turn of events and the community was rebuilt, ultimately establishing a thriving agricultural and milling economy in the years that followed.
Top 23 Things to Do in Simsbury, CT ❤️
Prior to exploring the natural wonders boasted by Simsbury, you'll want to fuel up! There are no shortages of places where you can grab either a homemade bagel egg n'cheese, a specialty latte, or baked goods.
First pick a cafe and fuel up for the day!☕️
1. Pop Over Eatery ☕️
Pop Over Eatery is a must-visit spot for brunch and coffee enthusiasts visiting Simsbury. With fresh, locally sourced ingredients and a warm inviting vibe, Pop Over's is an ideal pre-adventure (or post!) destination.
Their unique menu features creative dishes with their homemade popovers including the Protein Pop with eggs and cheese and the Veggie Pop with scrambled eggs, avocado, and goat cheese - yum! They also have traditional breakfast sandwiches, waffles, pancakes, or brunch bowls like chia seed pudding with fruit. 🙂
They have a full coffee bar and have very unique offerings that you can sip on there or take to go. Tip: It gets VERY busy here on weekends so make a reservation or call ahead to see about wait times! You can also plan to take your meal to go.
2. Coffee Spot
Nestled in a charming Victorian house at 750 Hopmeadow Street, The Coffee Spot offers a cozy and inviting atmosphere perfect for coffee lovers and casual diners alike. With individually themed rooms, fireplaces, and eclectic decor, it provides a unique setting to sip your favorite brew, enjoy a freshly baked pastry, or catch up on some reading. Whether you're looking to relax, work remotely, or meet friends, The Coffee Spot is designed to be your personal retreat in the heart of Simsbury.
Another option for bagel lovers ➡️ Brookside Bagels ☕️🥯
Brookside Bagels is an equally excellent choice for breakfast but a better choice than Popovers if you are in a rush. Brookside is not 'fast food' but you can order at the counter one of their homemade bagels with cream cheese or as a breakfast sandwich and get it to go faster than a sit down breakfast!
Farm Stops in Simsbury
Time to take your coffee to a farm and stroll! There are 3 different farms worth checking out in Simsbury. From a vineyard with a full produce market to a petting zoo and one that has homemade ice cream and family friendly trails to walk. Take your pick from the farms below!
3. Tulmeadow Farm
Also located in West Simsbury, Tulmeadow Farm Store offers fresh produce, dairy, meats, ice cream, and more. It’s a great stop for local ingredients if you want to bring farm flavors into your picnic or meals while in town.
4. Flamig Farm (West Simsbury)
Flamig Farm features a farm store open 9 AM–5 PM (April–November), where you can pick up their signature fresh organic eggs, local honey, and seasonal gifts. They also host family-friendly experiences like hayrides, visits with animals, and seasonal events.
5. Rosedale Farms & Vineyards
Right in Simsbury, Rosedale Farm & Vineyards is a historic working farm with a bakery, farm store, corn maze, and events (like chef-to-farm dinners) especially in their active season. Their property also includes a nature trail (1.1 miles) and native plant gardens.
📸Check Out Simsbury's Must See-Scenic Spots
6. Old Drake Hill Flower Bridge
One of Simsbury’s most charming and photographed landmarks is the Old Drake Hill Flower Bridge. Originally built in 1892 as a metal truss bridge spanning 183 feet over the Farmington River, it carried one lane of traffic until 1992, when a newer two-lane bridge was put in just north of it
🚗 Click for the Google Map location of the bridge located at Old Bridge Rd., Simsbury
7. Stratton Brook State Park
Stratton Brook State Park is one of Simsbury’s most peaceful outdoor escapes, known for its easygoing beauty and family-friendly atmosphere. Easy stroll or bike along shaded paved trails, swim or fish in the park’s tranquil pond, and enjoy a picnic surrounded by tall pines and gentle breezes. If I want an easy walk and pretty scenes, I head to Stratton Brook.
🚗 Click here to navigate to an entrance of Stratton Brook that leads you to Stratton Brook's most photographed - the bright red covered bridge. From the parking on the intersection of Town Forest & Stratton Brook Roads, walk northeast on the paved path and after 0.15 miles you'll arrive at the red bridge. With accessible paths and scenic viewsStratton Brook is the perfect place to wander and take photos!
8. Pinchot Sycamore
The Pinchot Sycamore is a majestic natural landmark in Simsbury and serves as the town's landmark! Located on the east bank of the Farmington River it's one of the oldest sycamore trees in CT and one of the largest! This huge American sycamore boasts a trunk circumference of more than 28 feet, a height over 100 feet, and a canopy spreading more than 120 feet wide.
🚗 Click here to navigate to the parking lot for the Pinchot Sycamore which is at the intersection of Hartford Rd and Nod Rd. This is also a designated canoe/kayak launch for the Farmington River!
🥾Top Spots to Walk, Hike, or Bike in Simsbury ⛰️
9. Talcott Mountain & Heublein Tower ⛰️
Heublein Tower atop Talcott Mountain is a local and regional favorite right here in Simsbury. The well-maintained trail systems lead you through lively forests and along precipitous cliffs, offering spectacular view and view of the Farmington Valley.
The most prominent of highlights on this adventure is Heublein Tower, a historic landmark that sits atop this trap rock mountain. From the tower’s observatory (Summer visiting hours, Friday - Monday, 10 am - 4 pm) with panoramic vistas that stretch for nearly 50 miles in all directions.
🚗 Click here to navigate to the main trailhead parking. Take the wide gravel path for 1.25 miles up to Heublein Tower then return the way you came for a total of 2.5 miles.
10. Nod Brook Wildlife Management Area
Another beautiful spot along the Farmington River, as so many in Simsbury are - Nod Brook WMA (Wildlife Management Area) is a must-visit place in Simsbury if you have a dog! Nod Brook is a 137-acre gem that is one of a kind as it's one of the only approved off-leash trail preserves for dogs.
Trails encircle this sprawling preserve and there's enough room where it never feels like there are a lot of people. There's a prime view of Heublein Tower, access to the Farmington River for the dogs, and a little pond where my dog, Captain, love to swim! Note: It is used for retriever-dog training so be sure to check the calendar as some weekend it may be hosting an event. Check the events calendar here!
🚗 Click here to access the Google Maps location of Nod Brook and from there you can hit 'directions'. The location and parking lot is kind of a secret and can be hard to find but click the link I provided then park at the top riht corner of the parking lot when you pull in (you'll notice office buildings on your left) and find the little trail that leads into the woods. 🙂
11. Farmington Canal Heritage Trail
The Farmington Canal Heritage Trail (sometimes called the Canal Greenway) is an 84-mile long paved path that runs right through Simsbury. This is a great spot for those looking for an easy walk with people of all ages, a paved path to push a stroller, or to ride bikes.
🚗 There are lots of different parking and access points in Simsbury but here are a couple: 22 Iron Horse Blvd (parking behind playground) and 99 Wilcox St.
12. Penwood State Forest ⛰️
Essentially across the street from the main entrance to Talcott Mountain, Penwood State Forest offers another perfect hiking experience in Simsbury. Spanning over 800 acres, the forest features diverse trails suited for all skill levels, from gentle sloping paths to more challenging rocky routes.
13. Hedgehog Mountain ⛰️
Hiking the trails at Hedgehog Mountain offers a rugged, classic hiking experience in Simsbury with several lookout points. There are different route and loops you can take here so check out my post ➡️ 2 Different Routes up Hedgehog Mountain to choose the trail that's right for you and to find more details!
🎶 Catch a Show or Live Music 🎶
14. Simsbury Meadows Performing Arts Center (SMPAC)
The Simsbury Meadows Performing Arts Center is a scenic outdoor venue that hosts a variety of concerts and events throughout the year. It’s best known as the summer home of the Hartford Symphony Orchestra and for the Talcott Mountain Music Festival, but it also features pop, jazz, country, and tribute acts. With its beautiful setting and lively community events, SMPAC is a favorite destination for locals and visitors alike!
15. Maple Tree Cafe
The Maple Tree Cafe, housed in an 1895 historic tavern, transforms into a vibrant music venue every Friday and Saturday night, with local and regional artists. From acoustic sets to full-band performances, the intimate atmosphere ensures an up-close experience with the music. The café's cozy interior and outdoor seating options provide a perfect setting to enjoy your favorite tunes alongside their renowned Italian cuisine and craft beverages!
Lunch or Dinner in Simsbury 🌯🍝
For those looking to enjoy a hearty meal and expertly crafted meal after a local endeavor in the wilderness, Simsbury has plenty to offer. Certainly tough to choose but here are three establishments that don’t miss,
16. Grassroots (casual)
Grassroots Kitchen + Creamery is an ideal lunch destination after a hike. It's casual and we often come here after a hike in Simsbury. Their diverse menu features global street food favorites like the Turkish Berliner wrap and Greek Chicken & Bacon Salad, all crafted from scratch daily.
Finish with their award-winning ice cream, recognized as "Best Ice Cream" in "Best of Hartford 2024."
17. Millwrights Restaurant and Tavern
Nestled beside a scenic waterfall in an old 17th-century mill, Millwright’s Restaurant and Tavern is one of Simsbury’s most charming dining spots. The setting alone makes it worth a visit — the sound of rushing water and the rustic mill architecture create an atmosphere that’s both elegant and cozy. Whether you’re seated in the fine dining room overlooking the falls or downstairs in the more casual tavern, the ambiance captures the perfect blend of Simsbury’s history and natural beauty.
The food is just as impressive as the setting. Millwright’s is known for its creative, locally inspired menu crafted by Chef Tyler Anderson, featuring seasonal ingredients sourced from Connecticut farms.
Ice Cream in Simsbury🍦🍦
18. Ice Cream in Simsbury
- Grassroots: Needn’t say too much more than "Best Ice Cream" in "Best of Hartford 2024."
- Tulmeadow Farm: A a superb spot featuring their homemade ice cream all with a scenic view. Take your ice cream to go for a walk on the farm trail (Tulmeadow Farm & Woodlot) right behind the farm store!
Simsbury Nightlife and Breweries
19. Almost Famous Brewing Company
Just over the Simsbury line in East Granby, Almost Famous Brewing Co. is a creative local hangout that hosts live music, events, and offers their own in-house beers and hard seltzers.
20. Talcott Mountain Collective
lawn games and spots to sit with a scenic view of Talcott Mountain, they offer craft beverage options on site (among other food, drink, and live music!). Dog-friendly 🐶
21. Thomas Hooker Brewing Co.
Thomas Hooker Brewing Co. — nextdoor in Bloomfield, CT, with a taproom and outdoor beer garden, offering a solid option if you’re venturing a bit farther out. Dog-friendly at their outdoor biergarten! 🐶
Enjoy Farmington River in Simsbury
This iconic waterway weaves its way through the town at several different points and provides both recreation and historical significance. The river played an important role in the early American industrial era, helping to power local mills and factories and today the river is a haven for outdoor enthusiasts. Its timeless beauty and ecological importance have justly earned it a designation as part of the National Wild and Scenic Rivers System.
22. Paddle or kayak on the Farmington River
The perfect thing to do in Simsbury on a warm day if you like to be on the water! Click here to check out all the spots you can put in a board or kayak to the flat spots of the Farmington River.
Explore an Abandoned Town
23. Discover Pilfershire Abandoned Town
🥾Yes, you heard that right! Walk the Pilfershire Abandoned Town Trail tucked away in the woods of Simsbury to get to what was once a thriving colonial settlement. Today, it stands as a testament to early American life, with remnants like stone walls, cellar holes, and deep stone wells scattered throughout the forest. The Pilfershire Abandoned Town Trail offers a 3.4-mile round-trip hike through this historic site, featuring two waterfalls and a peaceful, secluded atmosphere. Accessible via Firetown Road, it's a perfect spot for history enthusiasts and nature lovers alike.
Conclusion to Exploring Simsbury, CT
As you can see, there is SO much to do and choose from in Simsbury, especially if you're someone who appreciates good food and beautiful nature. With this list, you can fill a whole day of fun adventures here in Simsbury.
It's a scenic Connecticut town that seamlessly blends rich history with the natural beauty of the Farmington Valley.
Whether you’re exploring the trails of Talcott Mountain, learning about its colonial past, or enjoying the hospitality of its cafés and restaurants, Simsbury quite literally has something for everyone!
Feel free to leave a comment or question below about exploring Simsbury, I'd love to hear from you and see if there is a favorite activity that I left off this list!
Happy exploring!🐾💗🥾☀️
