Connecticut is known for its spectacular seasons and cute little towns.
But did you know that Connecticut also features abundant wildlife and some of the most beautiful landscapes in the country?
With colorful autumn months and lush, green summers, there are tons of opportunities for physical activity and recreation, where visitors can get out and explore the great outdoors during any time of year.
And there’s no better way to experience all that natural beauty than exploring the Connecticut hiking trails near Greenwich and nearby!
Just a short drive from Stanton House Inn in Greenwich, you’ll find some of the best state parks in CT. You’ll also find plenty of preserves, forests, and more that are ideal for a heart-pumping New England hike. And if it’s an easy drive from Greenwich, it’s just as easy to reach from New York City!
So grab your most comfortable pair of hiking boots (sneakers you don’t mind getting dirty will do in a pinch) and get ready for an adventure! Here are some of our favorite places to go hiking in Connecticut.
For a quick introduction to our 5 favorite Connecticut hiking trails near us, click below to watch our 1-minute video of the local hiking highlights:
Why the Hiking is So Great in Connecticut
I loved living in Charleston, South Carolina.
However, one of the many things I missed about living in New England and Connecticut more specifically was how close both the beach and hiking were to each other.
In Charleston, hiking with some elevation required a 4-hour drive to Greenville and the Upstate, which made it a weekend trip activity at best.
But hills stretch from the uplands of Connecticut all the way to the coast. Stanton House Inn is actually situated on the first ridge the rises from Long Island Sound on the Connecticut shoreline.
And the hills are a large part of why so much of Connecticut is wooded and wild, perfect for hiking and other outdoor activities.
Why? Read on.
A (Short) Recent History of the Natural World in Connecticut
For such a small, densely-populated, state, Connecticut has done a beautiful job of maintaining plenty of green spaces.
The reality is more than likely tied to the history of Connecticut.
When New England farmers finally gave-up on working the rocky soil of Connecticut and moved west in the 1800s, the soil reverted to scrubland.
Over a hundred years later, Connecticut has reverted to about 70% forest, 30% settled land. That’s a complete reversal of the numbers in the 1700s and 1800s, when the state was 70% farmland, 30% forest.
And that explains why you often see rock walls (and ruins of old homes) in the middle of forests here. No one built a rock wall through the forest; what appear to be old forests were cleared fields and pastures around 1850 or so.
Where To Go Hiking in Connecticut
There are some fantastic options throughout Connecticut. Our list is of the best Connecticut hiking trails near Greenwich, since that’s where we are.
Map design by Stanton House Inn
The Best Hiking Trails in Greenwich, CT
Greenwich has plenty of green space. Exploring all the parks and hiking trails near Greenwich, CT, would require more than a long weekend. Though an added benefit is that the trip from NYC to Greenwich is quick and gets you into the woods quite quickly.
Many of these parks made our list of the best free activities and things to do in Connecticut.
In order of distance from Stanton House Inn in downtown Greenwich:
1) Mianus River Park
Not to be confused with the Mianus River Gorge, which is further upstream, the Mianus River State Park straddles the Greenwich and Stamford borders. This State Park is large enough to get lost in, with a diverse array of environments, including the Mianus River.
An afternoon exploring the woods, swamps, and old farmstead ruins is well-worth the trip. And both towns have their own respective parking area, depending on which direction you’re coming from.
The Mianus River and neighborhood that bears the name is pronounced My-ahnis, by the way. Everyone in Greenwich has run into their fair share of snickering teenagers.
It’s a corruption of the name of a Native American chieftain, Mayanno.
2) Babcock Preserve
The seven-mile trail system at Babcock Preserve features three separate hiking loops that travel over old, overgrown roads and provide an easy walk through the forest. You’ll encounter a variety of trees and flowers along the way, and berry species like strawberry, blueberry, huckleberry, elderberry, and wild grape are abundant. Be on the lookout for curious native wildlife throughout your journey.
That said, as the largest park in Greenwich, it’s easy to get lost here.
But that’s half the fun.
The parking area is easy to reach, off of North Street, close to the Merritt Parkway.
3) Greenwich Point Park
This Sound-front park is a go-to destination for many outdoor activities. As one of the best Greenwich beaches, visitors can enjoy a day of swimming, picnicking, and kayaking, or venture out on one of the sandy hiking trails. You’ll also have great views of the water and even the Manhattan skyline from various parts of Greenwich Point Park, so be sure to bring a camera!
4) Montgomery Pinetum
Montgomery Pinetum and the adjacent Pomerance Park offer a sizeable expanse for hiking.
Some of the major points of interest in this park within walking distance of Cos Cob include:
- The central pond and views from the hills surrounding it
- The pinetum, or collection pine trees
- The ruins of the old mansion in Pomerance
This is the birthplace of the Boy Scouts of America, by the way.
Farther Afield Hiking Trails in Fairfield County, Connecticut
This list of Connecticut hiking trails and parks are listed by distance from Stanton House Inn in downtown Greenwich.
During the statewide Covid-19 lockdown, all our state parks and most local parks were closed to visitors.
The only thing left open to hikers were state forests, as they were much less well-known and less-visited.
So I got the opportunity to see an entirely new side of Connecticut!
Read on for our list of top hiking trails in Fairfield County, CT:
5) Bartlett Arboretum
Bartlett Arboretum and Gardens offers 93 acres of hiking trails, gardens, and wetlands.
Many of the flora in the collection are from New England. That said, you’ll find additions from all over the world, some planted as long ago as a century.
There’s no question it’s one of the best things to do in Stamford, CT.
And did we mention a visit here is also free?
6) Devil’s Den Preserve
Don’t let the name of this preserve scare you! At 1,756 acres, Devil’s Den is the largest piece of protected land in Fairfield County and contains woodlands, wetlands, and ridges that are perfect for hiking. While exploring the preserve, you may come across red fox, bobcat, coyote, Eastern copperhead, wood duck, ruffed grouse, pileated woodpecker, and many other fascinating species.
Devil’s Den is pretty easy for any skill level of hiker, but its big selling point is its relative proximity and its size–it’s a huge park offering some of the best hiking trails in Connecticut. Look at any map of Fairfield County, and that big green blob northeast of Bridgeport, CT is Devil’s Den.
There are more than a few vistas here with beautiful views of the surrounding woods. One of my most recent memories of this park is getting lost there for hours looking for a spectacular view overlooking the Saugatuck reservoir on the western side of the park.
I never found it the second time around, so let me know if and when you do.
With little bridges crossing the myriad streams, outcroppings interspersed to provide views above the incessant woods, sunny little ponds, and rock shelters, this is a fun park to get lost in on a lazy afternoon.
And when you’re done, stop into Nod Hill Brewery, one of the best breweries in Connecticut.
7) Centennial Watershed State Forest
Across the Saugatuck River from Devil’s Den Preserve is the Centennial Watershed State Forest.
This 15,300 acre forest centers around the Saugatuck Reservoir in Redding, Connecticut.
The Connecticut State Forest’s hiking trails offer some gorgeous views of the reservoir, as well as some intense uphill hiking.
8) Tarrywile Park
Tarrywile Park, in Danbury, Connecticut, has 722 acres. That makes it the largest municipally-owned town Park in the entire 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.
Stroll through the formal gardens, former dairy farm, and orchard and enjoy the bucolic appeal of the park. And be sure to check-out Tarrywile Mansion and the ruins of Hearthstone Castle.
Top Connecticut Hiking Trails near New Haven, Connecticut
There’s plenty more hiking once you cross the Housatonic River from Fairfield County.
In some cases, significantly more, as many parts of Connecticut are less densely-settled than Fairfield County.
New Haven and its environs are not a good example of that.
But there’s still some great hiking, either in state forests or state parks.
9) Naugatuck State Forest
In the Naugatuck Valley, about an hour’s drive from downtown Greenwich, is Naugatuck State Forest. The entrance to the forest is in Seymour, CT. It was started by Harris Whittmore, an industrialist who wanted to purchase land in the valley to donate to the state.
His family posthumously donated 2,000 acres about a decade after he started the project.
The highlights of hiking at this State Forest are the waterfalls.
10) Farm River State Park
Located on the Long Island Sound in East Haven, this 62-acre park offers beautiful views of salt marshes and relaxing seaside sounds. The CT hiking trails at Farm River State Park are short, but some off-trail exploration will lead you to scenic vistas that are worth the walk. Along the way, you’ll see egrets feeding in the marshland as well as a wide variety of ducks, gulls, and even blue heron.
11) Sleeping Giant State Park
The traprock mountain earned its name because its shape gives the appearance of a large, sleeping, person.
That person is possibly of the giant persuasion.
The hike to the tower at the top of the ridge is fairly easy, and the view from the tower is lovely. This is one of the most popular and most visited state parks in Connecticut for a reason.
Fantastic Hiking Trails in the Litchfield Hills
Cross the Housatonic River to the north of Fairfield County, and you’ll cross into Litchfield County.
The northwest corner of the state mostly corresponds to an area some visitors call the Litchfield Hills of Connecticut.
This area hosts some of the best CT hikes with a view anywhere in the state.
12) Lovers Leap State Park
Named after two star-crossed lovers, this state park straddles the Housatonic River.
Lovers Leap State Park offers sweeping views of the river, as well as meandering trails and historic ruins. Don’t miss taking a snapshot or two of the 1895 truss iron bridge that crosses the Housatonic.
13) Mine Hill Preserve
About an hour away from Greenwich in Roxbury, CT, Mine Hill Preserve has four miles of Connecticut hiking trails that run past old mines, granite quarries, and ruins of an iron-making complex. The popular Blue Loop Trail begins at the industrial site, climbs up the Donkey Trail past a reservoir, and continues past massive granite cliffs, eventually descending back to the Shepaug River valley.
Be sure to read the signage along the way to learn more about the area’s unique past.
14) Talcott Mountain State Park
Overlooking Hartford and West Hartford is Talcott Mountain State Park in Simsbury, Connecticut. This park is a bit of a drive, an hour and a half or more from Stanton House Inn, but it’s worth it on a nice day.
Talcott Mountain State Park is huge, but the main draw is one steep trek from the parking lot. The immediate reward for the ascent is sweeping views of the Farmington River valley. Continue further to approach Hueblein Tower.
This 165-foot tower has an interesting story. Gilbert Hueblein, a local magnate who made his money in hotels, restaurants, and newspapers in Hartford, hiked the ridge with his bride to be.
He promised her that he would build her a castle there, and decades later he made good on that promise.
The top of the Bavarian-style Hueblein Tower offers a panoramic view of Hartford and the surrounding area, making it one of the best hikes in CT with a view. It’s especially spectacular in the fall during peak Connecticut fall foliage.
Plus, when you’re done, you can check-out Simsbury, one of the cutest towns in Connecticut.
15) Haystack Mountain State Park
Another top pick for state parks in CT, Haystack Mountain State Park features a trail leading to a 34-foot observation tower.
Top Hiking Trails in Mystic Country
At the southeast of Connecticut, there are a few great CT hiking trails here, too.
It’s just a bit of a trek from Greenwich.
But if you’re feeling getting dirty after the quaintness of Mystic and Stonington, here are some great options:
16) Devil’s Hopyard State Park
Devil’s Hopyard State Park’s Chapman Falls is a wonder to behold in East Haddam, Connecticut.
At just 60 feet, the Eight Mile River has three drops cascading over the rocks into a calm pool of water where people frolic in the summer months.
The park is named after the local myth that the holes and rocky falls developed when the devil wet his tail and stomped his feet in anger.
While there are a series of trails to hike, many are quite steep and challenging.
If you’re up to it, you can find yourself overlooking an expansive valley, a worthwhile trip in peak fall leaf season. As mentioned, the waterfalls are the main attraction in the summer months, and people also come to photograph the wooden covered bridge.
17) Denison Pequotsepos Nature Center
This nature center has been providing guests the opportunity to experience local flora and fauna first hand for nearly 70 years.
A few of the attractions on-site include:
- Over 10 miles of hiking trails
- The natural history museum
- Exhibitions such as injured birds of prey like owls and hawks
And yet one of the most unique and mysterious attractions is a nearby archeological site that Denison Pequotsepos Nature Center has exclusive access to, as caretakers of the land.
Click over to our guide to attractions, activities, and things to do in Mystic, CT, for more information.
Enjoy Exploring the Best Hiking in Connecticut!
And that’s our list of the best Connecticut hiking trails across Connecticut.
A few more options around the state include the Blue-Blazed Trail system, if you’re interested. Find the closest trail as well as nearby parking areas on the Connecticut Forest & Park Association website.
Even if you plan on exploring these trails from the comfort of your armchair, we can’t wait to hear where the trails take you!
Check exploring our website for more free guides to Greenwich and nearby:
- Top hiking trails near us in downtown Greenwich, Connecticut
- The best state parks across Connecticut
- The top beaches lining the Connecticut shoreline
Updated and republished August 2, 2022