As the summer season heats up, we’re all yearning to spend time in the great outdoors. Our leisure time is gleefully filled with a host of fun activities – from kayaking to swimming, camping, biking, and hiking.

By now, the trees are covered in verdant green leaves and the flowers have blossomed in a rainbow of hues. It’s a great time to take to the trails for a long walk or a more challenging hike – whichever suits your style.

Great hikes abound – from New York’s Millerton, Copake, Rhinebeck, and Pine Plains to Great Barrington, MA, and Connecticut’s Canaan, Lakeville, and Sharon regions. So, get your hiking shoes on and go explore!

Starting in New York, Millbrook

Just a ten-minute drive from Millbrook is Dover Stone Church Preserve. Once used as a refuge by the Pequot Indians, the ancient, natural cavern provided a haven for Indians who were fleeing from the English army during the 1600s. The site draws its name from the cave’s triangular entrance, which resembles the shape of a steeple. Listed in the National Register of Historic Sites and Places, the bucolic property boasts three miles of nature trails. Go find your zen. Cool off at the waterfall. Camp out on the banks of the lake with a book. While here, you’ll witness the splendor of unique rock outcroppings, take in scenic vistas, and spot lots of fauna that hails from the West Mountain ridge.


Chase more waterfalls at Bash Bish Falls State Park – a two-mile trail that straddles New York’s sprawling Taconic State Park and South Egremont, MA. On a warm summer day, you can bask in the mist of the cascading waterfall – the highest single-drop fall in all of Massachusetts. The short hike, which ensures Instragram-worthy photos, is ideal for all skill levels. While there, explore the neighboring wilderness at Mt. Washington State Park.

Rhinebeck/Pine Plains

Just a short hike up Drayton Grant Park at Burger Hill – one of the highest points in Rhinebeck – will reward you with majestic views of the Hudson River and expansive surrounding countryside. To the west, you’ll see the Catskill Mountains and to the east, the Taconic Mountains. This serene spot is ideal for taking a leisurely stroll, picnicking, practicing yoga, or meditating.

Just four miles from Rhinebeck is Poets’ Walk Park – a 120-acre park located in Red Hook. Its name was inspired by the many writers such as Washington Irving who enjoyed rambling here. Listen to the enchanting song of colorful songbirds, traverse through the meadows, stroll the wooded ravine down to the Hudson River, and enjoy the sounds of rushing water. Poet’s Walk is an ideal place to curl up on a bench with a book, picnic, or cool off in the shade of the rustic gazebo.

Stissing Mountain is also located in the Pine Plains/Rhinebeck region. Its 1.8-mile trail offers a lakeside setting and picturesque views. The trail, which is rated as difficult, is primarily used for hiking, walking, nature trips, and bird watching. One of the biggest attractions is the Stissing Fire Tower, which also promises sweeping views. The shortest and easiest point of access is from Lake Road in Pine Plains, just down from the Thompson Pond Preserve entrance.

Columbia County/Hudson

Nature buffs can head to Greenport Conservation Area – a 736-acre site that includes seven miles of trails. The paths are primarily flat, which makes Greenport an ideal place for beginner hikers. The summer season is apropos for birdwatching and enjoying dining al fresco. The park, which is within walking distance of Hudson, also offers scenic views of the Hudson River and Catskill Mountain.

Starting in Connecticut, Norfolk and Falls Village

Great Mountain Forest, located in Norfolk and Falls Village in the northwest corner of Litchfield County, CT, a green space that offers more than 6,000 acres of contiguous forestland. Escape the chaotic world just beyond the woods. Here, you can enjoy long stretches of forest trails, which welcome both hikers and mountain bikers. A pioneer in forest stewardship, Great Mountain Forest practices sustainable forest management, promotes biodiversity and resilience to climate change, and supports education and research. Nature buffs can learn more on the non-profit organization’s website,


There are lots of fun things to discover at Kent Falls State Park.  Wander across the covered bridge or hike one of the falls. Explore the Kent Falls Trail, which winds one-quarter mile up along the falls. Although not a difficult hike, be aware that there’s a steep incline.

Less than a half hour drive from Canaan and about thirty minutes from Great Barrington is Haystack Mountain. It boasts a 34-foot high stone tower at its summit, which is perched 1716 feet above sea level. Indulge in spectacular views – from the Berkshires to the peaks in Massachusetts, New York, and the Green Mountains of Vermont. Travel the twisting roadway, which provides quick and easy access halfway up the mountain. Along the road, you’ll see delicate mountain laurel adorning the grounds. More adventurous folk can opt for hiking the rugged trail to the top.

Also near Canaan is Bartholomew’s Cobble – a natural wonder created by geologic upheavals. It was named for its two rocky knolls or “cobbles” that rise above the Housatonic River. Situated on the Massachusetts/Connecticut border, the landscape offers mountain vistas and panoramic views of the Housatonic River Valley. Boasting an enormous variety of woodland flowers and fern species, the Cobble’s diverse flora earned it a National Natural Landmark designation in 1971. Hurlburt’s Hill marks the property’s highest point. Ascending 1,000 feet, it uncovers a 20-acre upland.

A short drive from Canaan and Great Barrington is Lion’s Head Trail – a four-mile trail that is ideal for experienced hikers. Renowned for its dramatic overviews, wildlife and bird watching, it also offers access to Connecticut’s highest peaks. Along the hike, you’ll see a range of terrains from waterfalls to woodlands. From mid/late June to early July, you’ll enjoy the fragrance and beauty of a bounty of white and pink mountain laurel.

Before you head out, check for COVID-19 updates, hours of operation, and other details.