Notes: We usually park either at the Pinetum or nearby Bible Street Park (where there is a ‘back entrance’ trail). There is a third lot on Orchard Street, but it is small and often crowded.
So close to town but just a wonderful place to wander around with your furry friend. Both parks are pieces of former estates and offer a variety of trail types – from wide and paved to narrow paths through woods and marsh. Not to be missed; the ruins of Wyndygoul, home to Barbara Tuchman, author of ‘The Guns of August.’ One of Greenwich’s gems.
On your way home, stop off at Scarpelli’s and pickup some of their famous homemade sausage.
Notes: Parked in a small lot at the north end of Toomey Rd. right at the trail head.
A lovely hike up a mountain and back. Stopped for a lovely lunch at the top of the ski slope then continued to the summit. One downside, there is a road that goes to the summit so our peaceful hike was occasionally interrupted by loud motorcycles or car stereos as we neared the top. Even so, it was a beautiful hike, highly recommended for a warm fall day as the leaves start to change.
Notes:There are a few parking spaces along the road by the trail-head which is right at the CT/MA border. A larger lot is located about a 1.25mi south on Mt Washington Rd near the trailhead should you wish to do this hike in reverse.
I have wanted to do this hike for years: •Three peaks (Round Mountain, Mount Frissell and Brace Mountain)… •In three different States… •Plus the highest point in Connecticut… •As well as the New York / Connecticut / Massachusetts Tri-Point (where all three State borders touch)… •All in one 5.25 mile hike!
The first mile is the most difficult as you ascend Round Mountain (in CT) and then Mount Frissell (in MA), both of which afford beautiful views along the way. After you reach the summit of Mount Frissell you cross back into Connecticut at the CT Highpoint. A short trip down the trail is the NY/CT/MA Tri-Point where you will find a stone obelisk that marks the spot the three borders converge (although they left Connecticut off the marker for some reason!?!).
From Frissell’s summit it is a much easier hike along a ridge to the top of Brace Mountain in New York. The summit is very open with absolutely amazing vistas. After that it’s an easy and pretty downhill trail through the woods back into Connecticut ending at Mt Washington Rd. The last 1.25 mi is a dull but quick stroll along the road.
Recommended stop: If you came up Rt. 22 in NY, drop by McEnroe Organic Farm in Millerton for an excellent meal in their beer garden. We ate there and watched the sun set – perfect end to a wonderful adventure. http://www.mcenroeorganicfarm.com/
An amazing place for a fall hike with great views of the surrounding countryside. We hiked nearly the entire Blue Loop; parking at the Camp Office, we took the Yellow trail and then hiked the Blue in a counter-clockwise direction – it was about 6.7 miles.
The park is close to Kent, CT – a very pretty little New England Countryside town that is now filled with trendy (and expensive) galleries and eateries. We were going to stop for some coffee and pastries on the way out but the whole town was absolutely swarming with people! So take note if you plan on visiting with your hike – it gets very crowded on pleasant fall days.
Rock Scramble:If you go to the AllTrails review of this hike, you will see warnings of a difficult rock scramble section of the loop hike. These are not exaggerated. There is a very steep and rocky elevation change to be negotiated, including two 4-5 foot ledges that must be scaled up. Our pupper is a “big, strong, sturdy girl” – but she still needed two big boosts at those sections and ended up with a scraped up leg (I carry a human & doggy first aid kit in my day pack and recommend you do the same). If you have a smaller dog that can be lifted up or down, then it will be no problem. But bigger dogs will need to be OK with getting pushed/pulled over the ledges. It’s not impossible, but it’s difficult. Going up seems to be easier for the dogs than going down. You can avoid the scramble all together by doing an “out-and-back” hike to the summit of Cobble Mountain along the “Macedonia Ridge Trail.” Frankly, the Ridge Trail was the most scenic part of the park other than the the tip of Hilltop Pond (which can be reached by car for a quick scenic stop if you wish).
Activities: Walking, Hiking, Dog Socializing, Off Leash
Last Visit: 2020
Notes:A parking lot off Pemberwick Rd. was recently added. The meadow in the back is used by many local residents as an “unofficial off-leash area,” but this is not technically allowed and the field is not fenced.
Pemberwick park is our “home park.” We live a short walk away visit it frequently. The main portion of the park is comprised of a large baseball and soccer field adjacent to an enclosed basketball and tennis courts.
The charm of this park are its less visited trails and large meadow. As mentioned in the notes, the meadow located in the back of the park, past the playground along Pemberwick Road, is the local unofficial off-leash dog park. Many nearby residents take their dogs their early in the morning for a quick run. It’s important to note however that the only fence is along the busy road and it is in very poor shape with many breaks. If you intend to let your dog run here, please be sure you have it under good voice control and it’s common courtesy to use a leash if other people are present.
There are trails that run behind the fields and all the way to Weaver Street where there is a second small park. Despite the modest size (around 8 acres), this little wood is very lovely and quiet with a babbling brook running through the middle.
Notes:While many people let their dogs off leash in the park, be aware this practice is discouraged and Stamford has a dog warden / police officer that regularly patrols the park issuing warnings and tickets.
Nestled on the Greenwich-Stamford border just below the Merritt Parkway, the trio of parks (Greenwich, Stamford and State owned) together make up one of the largest wilderness spaces in the area. There are nearly 400 acres filled with a variety of trails – from wide carriage roads to narrow hiking paths. There is a little something for everyone… which means dogs owners should be extra careful as they are sharing the park with hikers, mountain bikers and the occasional horseback rider!
If you plan on exploring more than just the carriage roads, bring sturdy boots as some of the trails can get quite muddy in the spring. Also, don’t forget the bug repellent as the lowlands are a bit marshy.
Notes:Parking fees charged May – September, see website for details.
500+ acres of mostly manicured park jutting out into the Hudson River. There are many trails through the (smallish) wooded areas and scenic paths along the river. It gets quite crowded during the summer and there are often festivals or cultural events held there. Like Sherwood Island State park, there is also a small runway for model aircraft.
This is a lovely park with a large open area popular with picnickers surrounded by wide and well maintained hiking trails through the woods. The loop that goes up and over the dam is highly recommended.
As with some of the other parks on this list, the Old Croton Aqueduct Trail is adjacent (I believe it originates here) and I recommend hiking it for a while as it runs along some scenic high-ground.
Notes:Beaches in Maine and Acadia National Park are open to dogs mid-September through mid-May. Check the town or Park Service websites for more info.
Acadia National Park bills itself as one of the few dog-friendly National Parks. Neighboring Bar Harbor also has a reputation as a dog-lover’s Mecca. Neither disappointed.
We decided to take a vacation our dog could join us on and settled for Acadia and Bar Harbor. We love hiking and exploring with our mutt and this seemed like the perfect destination. With a little planning and research we found activities and destinations for the entire trip that were all dog friendly.
We headed out in mid-September when the beaches in Maine and the National Park were closed to swimmers but open to dogs. In addition, the summer crowds had thinned substantially and prices were cheaper. Traveling in “shoulder season” has it’s perks. The weather was perfect: high 70’s during the day, cool-crisp evenings perfect for sitting by the fire pit.
The drive is long but can be broken up with stops at many of Maine’s picturesque sea-side towns. Many had coastal walking trails or great little downtown shopping areas (though some were a bit tourist-y). We made stops in York, Ogunquit, Kittery, Freeport and Kennebunkport.
Bar Harbor is, as mentioned, super dog friendly. We had no issues finding a hotel that allows pets. Most restaurants have outdoor seating on a patio or deck where you can eat with your dog. There was even a dog-themed coffee shop.
The park and the surrounding islands are filled with miles upon miles of trails for hiking or walking – including the famous carriage roads. You can test your dog’s sea-legs on one of the mail boats that goes between Northeast Harbor and the Cranberry Islands. And, if you go off season, there are some amazing beaches to stroll down.
Not to be missed: Stopping at Jordan Pond House Restaurant inside the park for one of their world-famous pop-overs. There is outdoor seating that is dog-friendly. Lollipop lucked out the day we visited: it was windy and a tray of pop-overs got blown onto the ground. The servers split them up among the many happy visiting dogs.
Not to be missed: Sunrise on the summit of Cadillac Mountain. Due to fog / overcast weather, it took us three pre-dawn trips, but on the last day it cleared and was spectacular. Get there well before sunrise as it gets quite crowded at the summit parking area.
This is a hidden gem of over 150 acres with beautiful trails cut throughout. Especially nice are the adjacent private gardens open to quiet hikers. Well worth the trip, Westchester Land Trust is to be commended for opening their properties to people and their four-legged friends!
Notes:Very buggy in the summer, recommend visiting in the fall or winter. Trails can get very muddy.
This is a large preserve with over 7-miles of trails situated just north of the Merritt Parkway. Truth be told however, we rarely visit. On our first couple of trips we found the combination of deep-woods and marshy terrain equated to a higher than normal concentration of mosquitoes and biting flies. We are long past due for a return visit because of this, though it should be very pleasant in the winter when the mud freezes and the bugs are long gone.
Notes:Technically a Westchester County Park Pass is required but we have never had an issue in the off-season. Parking fee for picnic area only, May through September.
A 700 Acre park (including an 18 hole golf course) on the Mamaroneck / Scarsdale border that is conveniently located off the Hutchinson River Parkway. Despite being in a heavily suburban area the woods are surprisingly deep and quiet here. We typically visit in the fall / winter to avoid parking fees and crowds at the pool area.
PS – There is a wonderful mini-golf course by the pool where my father, brother and I used to battle it out in some highly competitive games.
Notes:Visited on a busy weekend and ran into a lot of people ignoring the leash law – so unfortunately it could be a problem for reactive dogs.
This is a very nice park – great variety of terrain; from hilly paths through the woods to a long paved “rails-to-trails” section of the North County Trailway that includes a scenic bridge over the Croton Reservoir.
As mentioned in the notes – we visited on a fairly busy day, parking was overflowing (we parked on an embankment on the side of the road) and the paved paths were crowded, but once we got out into the woods it emptied out.
This is certainly worth the trip, we did a 4.5 mile loop and there was still quite a bit left to see.
Activities: Dog swimming, hiking, dog socializing, walking, off leash
Last Visit: 2019
Notes:Off leash dogs permitted on trails and in the lake outside of the “100-foot” zones surrounding the parking lots.
This is truly a gem worth the trip. 170 acres of trails surround a brook that flows through a scenic cascade into a beautiful man-made lake. Easily accessible off the Meritt Parkway, you can park at either end of the lake though I recommend the paved lot close to the main beach (dogs not allowed but they do let you use their bathrooms). From there you can access easy paths to the popular dog-spots on the East side of the lake.
There are a few hazards to be aware of. First, the lake gets very deep very quickly (it is an old gravel pit) so be careful where you step. Second, there is a bit of a current – not so much it will sweep a dog away, but I have lost some toys to it. Finally, be careful of surly fishermen (unfortunately I ran into one once) and cut-lures with hooks they sometimes leave behind.
Activities: Walking, dog socializing, hiking, off leash
Last Visit: 2020
Notes:*There is now a $10 fee for parking.* There is a small off-leash area for dogs but it is unfenced.
This is a lovely park situated right on the Norwalk-Wilton border. It is a fairly big property (220+ acres of trails) surrounding a mansion. The grounds include a disc-golf course, a large lawn and a large network of paths through the surrounding woods.
Notes:(From website) Off-leash dogs, under voice control, are allowed only between dawn and noon. Leashed dogs are welcome from dawn until dusk.
Unlike Greenwich, New Canaan Land Trust has most of their properties open to visitors. We attended a small Adopt-a-Dog event here in 2019 and took the opportunity to tour their preserve. It is not very large (42 acres) but there are nice trails throughout. The day we were there they were being improved and expanded by local scouts. It was a nice wooded area with some hilly terrain and a small brook flowing through a pond. Worth spending around an hour exploring if you are in the neighborhood.
This location is mostly in Armonk but the entrance is most easily reached from the Greenwich side.
Donated to The Nature Conservancy, this 94 acre tract of land sat unused and neglected until the diligence and generosity of the Greenwich Riding and Trail Association got it transferred to them for equestrian use. Luckily, many of the horse owners are also dog lovers – so they opened the property to their canine friends too.
There are wonderful trails throughout the property – ranging from narrow paths through woods, muddy trails along some lakes and vernal pools to basically paved roads through expansive meadows.
When we visited we didn’t run into any horses but we did enjoy ourselves on some of the equestrian obstacles that dot the property.
Because this is basically private property and we are guests, please be very respectful and always keep your dogs leashed and pickup and carry out any poops.
A fantastic day-trip with lots of options – you can take a short stroll around the the welcome center and nearby lake, a longer walk through the surrounding rolling hills, visit the nearby working farm or make the trek all the way to the ruins of Rockwood Hall which offers beautiful views of the Hudson River. The sprawling network of trails connects with the Old Croton Aqueduct Trail that runs for miles from Croton-on-Hudson to Yonkers. If you hike to Rockwood Hall you will see remnants of the old aqueduct in the form of stone ventilation towers.