One of our favorite places for precisely this combination of scenes and experiences is Brattleboro, VT.  (That it happens to be where we met in 1999 notwithstanding!) Nestled in the southeast corner of Vermont, it is an easy 3.5-hour drive from New York City and if you have the time, Amtrak’s Vermonter line will get you there in just under 6 hours.  

 

Traditional Hikes

 

 

It’s almost too good to be true that a 15-minute walk will take you from Brattleboro’s quaint, thriving Main Street, to the base of a 1,335-foot mountain—Wantastiquet Mountain, which is technically in New Hampshire. To get there, enjoy a stroll down Main Street and cross the small steel bridge that carries Route 119 over the Connecticut River.  Make a left onto the first dirt road you see, and the trailhead is to the right.  

 

There are two ways to scale Wantastiquet, and both are moderately challenging.  First is by following the wider switchback trail that wends up the mountain. The ascent is fairly gradual and certainly better for younger children.  The second option takes you straight up and essentially cuts the hike in half timewise, one hour versus nearly two. Either way, the panoramic view at the top is well worth the effort!

 

If a more leisurely stroll is on order—especially for toddlers or babies in strollers—you have two options.  You can take a left from the parking lot and enjoy a longer and mostly flat hike along the dirt path that follows the Connecticut River. Alternatively, if time is of the essence, you could pass by the dirt road and continue along Route 119 to snap a picture at the sign that designates the New Hampshire state line. Photos at border crossings are an enduring thrill for our children, ages 11 and 8.  

 

At the other end of Main Street, just off the Brattleboro Common, are the Retreat Trails. This extensive network of relatively easy trails, many over a century old, covers 11 miles.  Follow Park Place to Linden Street, and take Timber Lane about 1,200 feet to your left.  There is no right or better way to hike along these trails—just enjoy whichever way you wander. 

 

Urban Hikes

 

The hilly landscape of the town center is also very conducive to an urban stroll. Over the years, the sidewalks have been improved with the addition of light-controlled crosswalks at key intersections. The tiny trickle of car traffic (at least by New York City standards) flows for the most part only down the main avenue, Main Street. The streets of Brattleboro are a wanderer’s delight, with numerous well-established shops selling everything from hiking and camping gear to syrup and moose-bedecked t-shirts. There are also two large and reliably great antique stores that have reasonable prices, and a growing number of excellent restaurants and cafes.

 

The centerpiece of Brattleboro Common is a gazebo that the children have enjoyed in various ways over the years.  It seems like yesterday that Halina was crawling up the stairs, and now she holds command performances from on high.  And for his part, Riley enjoys shimmying around the outside of railing—now that he finally can do it.  He also likes to come equipped with a butterfly net to catch and release as many fluttering friends as possible on the walk there and around the grounds.  

 

The Cherry on Top

 

For sentimental reasons our visits to Brattleboro always include a trip up to the campus of the School for International Training. It’s a bit of a distance from downtown, primarily past an unattractive row of strip malls, so we generally drive. Main Street, which doubles as Route 9, turns into Putney Road.  Just past the Hannaford’s supermarket, take a left of Black Mountain Road. The road up is a steep near-vertical incline that brings you to a summit where the view of the valley below is breathtaking. Up here there are lots of dirt roads and trails to hike around, all of which loop back at one point or another to the grounds of SIT. Go one evening to view the sunset—you won’t regret it!