This small town west of Hartford has an impossibly beautiful location, embedded in the Farmington River Valley up against the Metacomet Ridge.
The ample woodland and majestic overlooks combine to make Simsbury one of the best places to experience Connecticut’s foliage in Fall.
Heublein Tower, constructed for a wealthy businessman more than a century ago, is both a monument to behold and an awesome vantage point, taking in a huge slice of New England atop Talcott Mountain.
Simsbury was settled in the 1670s and as recently as 2015 was listed by Money magazine as one of the 10 best places to live in America.
1. Heublein Tower
In the 1910s the beverage magnate Gilbert F. Heublein built himself a summer retreat in the shape of a Bavarian castle.
Posted atop Talcott Mountain on the Metacomet Ridge at a height of 290 metres, the Heublein Tower cuts a familiar shape on the horizon west of Hartford.
The tower is 50 metres tall and was designed to be able to withstand winds of 100 mph.
You can reach this landmark on a yellow-blazed hiking loop from the parking lot on Summit Ridge Drive, 1.25 miles in length and taking just over half an hour to complete.
Heublin Tower is open between Memorial Day and the end of October, generally Thursday through Monday.
There are extended opening times in October when the tower affords sensational panoramas of the Fall foliage, and in this month you can visit every day of the week except Tuesday.
A massive swathe of Connecticut is rolls out before you at the observation platform, from Long Island Sound, up past the Hartford skyline, as far as Mount Monadnock, 80 miles to the north-east in New Hampshire.
2. Talcott Mountain State Park
The state park below protects more than 500 acres of wilderness on the linear Metacomet Ridge.
This basalt fault, 100 miles long, runs north to south through Connecticut from Long Island sound all the way to the Massachusetts-Vermont border.
Talcott Mountain is 13 miles in length and as with other landforms on the ridge has some unusual plant species because of its hot, dry ridges, growing chestnut oaks and eastern red cedar on the barren cliff edges.
Within the park are two waterfalls, awesome cliff-top lookouts over the countryside to the west, a highland swamp boardwalk and large bodies of water.
The 50-mile Blue-Blazed Metacomet Trail traces the ridge of Talcott Mountain, mostly running parallel to the yellow trail up to Heublein Tower.
3. Old Drake Hill Flower Bridge
There’s a stirring piece of heritage crossing the Farmington River Simsbury, in the form of a steel Parker truss bridge constructed in 1892. This is one of only three bridges of its kind still intact in the state and has a span of 53 metres and a roadway 3.7 metres wide.
When a new two-lane bridge opened in 1992 the Old Drake Hill Bridge became a footbridge.
A couple of years later it was spruced up with flower gardens growing annuals and perennials at each end, and wooden flower boxes flanking the roadway.
The Flower Bridge has become an icon for Simsbury, and both a backdrop for wedding photos and a vantage point for crew boat races on the river.
In 2019 the bridge was temporarily closed as the land on the west side was being transformed into a new park with a fountain, pavilion, river access and walking paths.
4. Simsbury Historical Society
In the heart of the town at 800 Hopmeadow Street, the Simsbury Historical Society is on a two-acre plot preserving 16 historic buildings in neat gardens.
The grounds and gardens are constantly open for you to look around, while guided tours of the showpiece Phelps Tavern are given Thursday to Saturday at 13:00 and 14:30. These begin at the modern Ellsworth Visitors Center, which was raised in 1966. In this building there are also interesting rotating exhibitions sourced from the society’s collections of furniture, decorative arts, textiles, costume, paintings and objects relating to Simsbury’s Ensign-Bickford Company, which manufactured fuses and blasting products.
Also at the Visitors Center is a play area for wee ones, with vintage wooden toys and period costume to dress up in.
5. Phelps Tavern
The main attraction at the Simsbury Historical Society is this house and tavern dating back to 1711 and expanded 70 years later.
The property was owned by the Phelps family for five generations over 200 years, but is named for Captain Elisha Phelps, who played a role in the Capture of Fort Ticonderoga in 1775. The tavern was in business from around 1786 to 1849, and was donated to the Simsbury Historical Society by Mary Phelps Ensign Lovejoy in 1962. You’ll go back to the tavern days inside, checking out a series of period rooms combined with interactive exhibits and broader details about the role of such establishments in New England in the 18th and 19th centuries.
6. Simsbury Center Historic District
Seven blocks of Hopmeadow Street in Simsbury’s town center are designated a Historic District, taking up more than 70 acres.
This includes the Simsbury Historical Society, along with a host of other monuments ranging in style from Colonial to Early Republic, Late Victorian and 20th-century Colonial Revival.
Some of the contributing buildings are the Simsbury Free Library (1887), the Colonial Revival Eno Memorial Hall (1932) and the First Church of Christ at 689, which has stood here in some form since 1697. At Railroad and Station Streets, the Simsbury Railroad Depot dates from 1875 and bears some of the Italianate flourishes that were fashionable at the time.
The oldest property of all is Simsbury Cemetery at 755, established in 1688 on the site of the town’s first meeting house.
7. Stratton Brook State Park
Just over 20 years ago Stratton Brook State Park became the first state park in Connecticut to be made completely accessible to people with wheelchairs.
In June, July and August people descend on the park to swim in the pond on the brook and take picnics under the surrounding white pines.
There’s a bikeway here on the trackbed of an old demonstration railroad, traveling across picturesque little streams.
A noteworthy building in the park is the Massacoe Forest Pavilion, constructed in 1935 by the Civilian Conservation Corps, a voluntary public work relief program.
Fishing is available year round, and when the park’s trails are snowed over they’re adapted for cross-country skiing.
8. Rosedale Farms & Vineyards
Now into its fifth generation, this farm has been growing top-quality produce for more than a century.
It would be impossible to list all of the fruit and vegetables available seasonally at the farm stand, but for the briefest summary there’s rhubarb, berries, carrots, cucumber, eggplants, peppers, potatoes, pumpkins, broccoli, peaches, watermelon and cantaloupe.
In summer there’s a sunflower maze to solve, and the stand has a range of delicious pies baked from scratch using ingredients from the farm.
The vineyards grow red grapes like Marquette, St. Croix, Merlot, Pinot Noir and Sangiovese, and whites like Bianca, Meynieu, Seyval Blanc, Chardonnay and Traminette for a line-up of award-winning wines.
You can stop by all summer up to the end of October to enjoy a bottle paired with local cheese or treats from the farm stand.
9. The Storyteller’s Cottage
A one-of-a-kind attraction, the Storyteller’s Cottage is many different things, all in a picture-book Victorian house, and all with a literary theme.
Just for a taste of what’s on the menu, there are storytelling workshops, vintage literary-themed parties, murder mysteries, evenings with authors, writing classes and clubs for kids who love books.
The Great Scott! Mystery Rooms are also here, boasting a set of three escape rooms that throw you into the worlds of famous works of literature.
For an idea of what the literary parties involve, in September 2019 there was a posh afternoon tea with scones, clotted cream and dainty sandwiches to celebrate the premiere of the Downton Abbey movie.
10. Pinchot Sycamore
Near the foot of Talcott Mountain on the east bank of the Farmington River grows the largest tree in the state of Connecticut.
When it was last measured in 2016 by the Connecticut Botanical Society this monumental American sycamore had a trunk 8.5 metres in circumference with a height of 30 metres.
The canopy diameter was a little less than 40 metres.
The tree is named in tribute to Gifford Pinchot (1865-1946), a leading figure in conservation in Connecticut and the United States.
The tree is thought to be at least 200, but is possibly more than 300 years old.
11. Simsbury Meadows Performing Arts Center
Out in the bucolic Farmington Valley countryside is a state-of-the-art outdoor venue for concerts under the night sky.
This is the second-largest outdoor stage in Connecticut, with a capacity of 10,000. The Hartford Symphony Orchestra relocates to Simsbury Meadows in the months of June and July, in time for the Talcott Mountain Music Festival.
Meanwhile a whole spectrum of contemporary artists takes the stage for the Summer Concert Series between June and September (the Beach Boys performed the week we wrote this article). Septemberfest is a family event now in its fourth decade, with food trucks and a whole program of live music over three evenings on the first weekend in September.
Simsbury has been designated a Bicycle Friendly Community by the League of American Cyclists, and you can pedal off on quiet town roads or traffic-free greenways like the Farmington Canal Heritage Trail.
This route is on the course of a canal turned railroad in the first decades of the 19th century to link New Haven with Connecticut and New England’s interior.
Simsbury has plotted a 14-mile loop that you can find on the Town of Simsbury website.
It’s also no trouble to rent or borrow a bicycle here.
You can get hold of a pair of wheels for a day or more at the Bicycle Cellar (532 Hopmeadow St. ). Simsbury Free Bike meanwhile is a bike share program allowing you to borrow a bike for 24 hours with a $10 deposit.
13. Flamig Farm
Recognized by the enormous sign reading “EGGS” backwards on its barn, Flamig Farm has a history dating back to 1907 and has been put to many different uses over the last century.
The farm store is open April to November, selling eggs of course, as well as a range of handmade toys and clothing.
In the summer Flamig Farm is also a visitor attraction for littler family members.
There’s a petting zoo with all sorts of cute animals, like goats, ponies, miniature horses, llamas, potbellied pigs, rabbits and a golden-headed pheasant named Larry.
Kids can also take pony rides, while families can even book a stay at the farm’s cosy lodgings.
Flamig Farm is famous for its spooky Halloween hayrides, and springs to life again in the build-up to Christmas when Santa calls in.
14. Roaring Brook Nature Center
This nature museum and sanctuary opened as long ago as 1948, and in the 1960s was gifted the adjacent Werner Farm, over 100 acres.
At Roaring Brook you can peruse permanent and changing exhibits on the local landscape and wildlife, view a replica Eastern Woodland Native American longhouse and check out a beaver wetland exhibit.
The center keeps a small collection of animals, like birds in outdoor flight cages, and has colourful outdoor gardens alive with wildflowers, butterflies and birds in spring and summer.
Roaring Brook also looks after five miles of trails disappearing into the neighbouring Werner’s Woods, and you can get hold of trail maps and wildlife checklist at the center’s store.
There are “Discovery Days” tailored for students, seasonal guided nature walks for all ages, as well as summer concerts and a “Hobgoblin Fair” at Halloween.
15. Simsbury Farms Golf Course
You’ll have to travel a long way to find a public course as good as Simsbury Farms.
These 18 holes, regarded as some of the best in the region by the New England Journal of Golf, were plotted on the site of a former orchard at the turn of 1970s The course architect was the fabled Geoffrey Cornish, and the rollercoaster terrain will catch you by surprise with some striking views.
With its sharp elevation changes, narrow fairways, water and bunkers, Simsbury Farms poses a challenge for golfers of all levels, and comes with a new clubhouse, a generous practice green and a driving range.