16 of the Best Connecticut Hiking Trails Near Greenwich

trees along one of the connecticut hiking trails near greenwich ct and nycConnecticut 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

waterfall in mianus river gorgeFor 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.

The Best Hiking Trails in Greenwich, CT

Greenwich has plenty of green space, and exploring all the parks and their respective hiking trails would require more than a long weekend.


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:

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.


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.

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.

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!

Audubon Greenwich

For incredible wildlife viewing and Connecticut hiking trails, Audubon Greenwich is ideal. The main sanctuary has seven miles of trails for guests to enjoy that venture through hardwood forests, old fields, lakes, streams, and vernal pools. Wildlife enthusiasts also love visiting the sanctuary to see river otters, muskrats, wood ducks, white-tailed deer, coyotes, flying squirrels, nesting bluebirds, wild turkeys, bats, and a wide array of reptiles and amphibians.


Head up the scenic Riversville Road to the picturesque little hamlet of North Greenwich to find the Audubon’s welcome center. The hiking trails slope into the park behind the center.


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 Connecticut

hiking trail in bear mountain state park, one of the best hiking trails near greenwich ct and nycThis 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!

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 up north 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 Connecticut breweries.

Centennial Watershed State Forest

centennial watershed state forest in redding, an option for hiking trails in connecticutAcross 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.

Naugatuck State Forest

frozen waterfall in naugatuck state forest, along one of the best connecticut hiking trailsIn 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.

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.

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 past.

Talcott Mountain State Park

hueblein tower against the sky in talcott mountain state park, an option for hiking trails in connecticutOverlooking 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. 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.

Hiking Trails in New York State, near Connecticut

More than a few of these options are closer to Greenwich and Stanton House Inn than many hiking trails in Connecticut.


We’d be remiss not to mention some of the great parks and trails managed by Westchester County or the New York State Park system!


In order, again, of distance from Stanton House Inn:

Rye Marshlands

Considering how fantastic this park is, it’s amazing that it’s not better known. I only discovered this park in 2018!


Rye Marshlands has about 3 miles of trails through woods, meadows and trails down to the forest and marshes of the harbor and Long Island Sound.


From the cliffs, there are some beautiful views of Rye harbor that the trees surrounding you perfectly frame.


And at a distance of about a 25-minute walk from the Harrison train station, it’s one of the easiest options for hiking trails near NYC by train!

Mianus River Gorge

mianus river gorge, an option for hiking trails near greenwich ct and nycJust over the border from Greenwich in Bedford, NY, is the Mianus River Gorge. It’s the only patch of old-growth forest remaining this close to New York City!


The trail stretches along the Mianus River as it passes through a gorge (as the name implies) and out into a reservoir that supplies the area with drinking water.


The area has been kept in pristine condition to keep our water supply pure, which ensures some great hiking. It’s easy to forget how close you are to a major metropolitan area when you’re far enough along the trails.


The whole trail is about six miles of moderately-difficult terrain with very well-preserved trails, which would likely take the average hiker about two and a half hours. My favorite parts of this park are the trail markers showing things both typical of the area and things extraordinary.


Keep in mind that dogs are not allowed here, as the main focus of this park is the preservation of local wildlife populations, which are generally not fans of canines.


While you’re up there, I highly recommend stopping-in to the picturesque downtown of Bedford.

Ward Pound Ridge Reservation

The largest park in Westchester County, New York, at 4,315 acres, Ward Pound Ridge Reservation offers an abundance of trails, views, and opportunities to get lost. And it’s only 30 minutes from Stanton House Inn!

Rockefeller State Park Preserve

hiking trail in rockefeller state park preserveA gift to the state of New York from the Rockefeller family, the Rockefeller State Park Preserve in beautiful Pocantico Hills, NY, offers plenty of hiking trails to explore.

This park offers a more bucolic experience. The Rockefellers designed their carriage trails to pass through a mix of forest and farmland. These carriage trails turned hiking trails create a hike that feels like something out of Europe.

It’s a unique experience in this modern era to walk through the woods and enter a clearing to find a herd of sheep placidly grazing next to their friendly herding dog.

Once you’re done hiking, you can check out the Rockefeller Art Gallery as well as all there is to see in Pocantico Hills and Tarrytown.

Bear Mountain State Park

view of the hudson river from the top of bear mountain in bear mountain state parkHome of the famous Oktoberfest at Bear Mountain festival, this State Park offers a series of trails that are just waiting to be explored.


Bear Mountain State Park’s for the real hikers. Located about a 45-minute drive from the Stanton House Inn in Bear Mountain, New York, this park can be pretty strenuous, with a rather steep hike up the hill to join part of the Appalachian Trail. The first section of the Appalachian Trail was originally constructed as a Bear Mountain State Park hiking path, and a current loop extends to the modern-day trail. Another popular trail passes by the Perkins Memorial Tower and offers spectacular views and rich history.


Bear Mountain State Park hiking trails do offer a spectacular view of the Hudson River, Peekskill, and the road to West Point.


While we admit this park is not actually in Connecticut, it’s still some fantastic hiking, and just over the Hudson River in New York State.

Hudson Highlands State Park

view from a hiking trail in hudson highlands state parkHudson Highlands State Park is another massive park in our area. But an added benefit to this particular park if you’re in New York City is that it’s accessible by the Hudson train line. Considering how remote parts of the park feel, it’s surprising to think that it’s only an hour drive away from Greenwich and Stanton House Inn.

That said, its accessibility is not its only draw.

The portions that make-up this park stretch from Peekskill in Westchester County up to Beacon, NY, in Dutchess County.

There are some breathtaking views of the Hudson River, as well as some cool ruins, holdovers from when the park was a cluster of old estates.

While you’re up visiting Hudson Highlands State Park, be sure to check out some of the Hudson Rivertowns, like Cold Spring, Peekskill, and Beacon.

Enjoy Exploring the Best Hiking in Connecticut!

And that’s our list of the best Connecticut hiking trails near downtown Greenwich and Stanton House Inn.

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:

Updated and republished March 16, 2021