For our main post this week we bring you the story of a hike in a corner of Connecticut called the Litchfield Hills – one of New England’s hidden treasures. Far from the famous shoreline or the insurance capital of Hartford this area is both historical and wildly scenic – as you’ll discover.

The hike was taken and told by Michael DiGioia, a native of Connecticut, and it makes me want to dust off the boots of last year and get cracking on hikes not yet done – and this is one.

Bear Mountain Hike – Michael DiGioia

When I close my eyes and picture Connecticut, my visions are immediately drawn to the miles and miles of pristine shoreline and sandy beaches that have been carefully carved by the Long Island Sound. Having lived my entire life along the Connecticut coast, I’ve grown to admire its serenity and peaceful charm.

Thoughts of panoramic mountaintop views are generally reserved for our New England neighbors to the north. The mythical appeal of the New England hiking scene has long been framed by the vivid image of sitting perched on a mountain, peering out at the scenic backdrops and vast landscapes offered by the Green Mountains of Vermont and White Mountains of New Hampshire.

Day Hikers in Connecticut, however, needn’t travel to Vermont or New Hampshire to enjoy a taste of this rugged outdoor beauty.  Lying in the Northwest Corner of the state, the Litchfield Hills boast an impressive and often overlooked collection of trails that allow a slice of this imagery to be experienced a little closer to home.

For many, the jewel of this network is Bear Mountain. Bear Mountain stands an imposing 2,316 feet and owns the distinction of being the highest summit in the state.(The honor of the highest point in Connecticut belongs to nearby Mt Frissell, an area not accessible to hikers).

Located at the foot of the Berkshires, the mountain delicately balances challenge with tranquility, as the sometimes strenuous hike to the top is rewarded by majestic vistas that on a clear day can extend into New York or Massachusetts.

A few weeks ago, my fifteen year-old nephew and I took our first trip up to the mountain. Our unquenchable thirst for new experiences combined with the satisfaction achieved from completing a good mountainside hike had planted a seed resulting in the birth of our latest adventure-to scale the individual high peak of each New England state. As the highest summit in Connecticut, Bear Mountain represented the first mission on our quest.

The two of us settled on the Undermountain Trail as our choice to ascend the mountain. Well-known among Connecticut hiking enthusiasts, the Undermountain Trail intersects with the famed Appalachian Trail and is generally regarded as the most popular route to the summit. The trailhead is located directly off Route 41 in Salisbury and can easily be missed, especially if while driving along the road your mind becomes captivated by the picturesque surroundings. Several times I have visited the area for hikes deeper into Massachusetts and New York, and I still often find myself taken by the scenery.

Roughly three miles each way, the Undermountain Trail proved to be a well-marked and well kept trail. The round trip journey took us about four hours to complete, but this estimation is by no means exact; the difficulty and time will vary based upon the objectives and experience of the hikers. Our particular hike included several photo-ops (one can never have too many pictures of the classic “Hiker Pose”) and a quick stop for lunch at the summit.

Both my nephew and I consider ourselves to be intermediate level hikers, and while we found the trail to be a worthy challenge, at no point did it feel overwhelming.  It does, however, require a certain amount of preparation and is not suited for everybody. Early on, we came across a mother and her young daughter just getting started on their ascent. Neither looked prepared for a strenuous hike, and my initial thought was that Bear Mountain was not the wisest selection for a child or novice hiker.

A couple of hours later my suspicions were confirmed – on our descent from the summit we again crossed paths with them, struggling mightily but still gallantly determined to conquer the mountain.

Once started, the immediate feeling of blood pumping through our veins served as our introduction to the trail. Elevation is gained early and often through series of steep and fairly challenging inclines. The initial portion of the trail is largely carved through forest, (Bug spray is a must for this hike), and though this section presents very few scenic opportunities, the tree-lined surroundings can offer a welcome respite on a hot day by gently providing cover from the bright sunshine above.

Eventually, the trail levels off, and after about two miles meets up with the Appalachian Trail. At the intersection, the presence of the AT is boldly announced courtesy of a very large and nearly impossible to miss wooden sign. Given its legend, the outsized marker seems appropriate; it’s hard not to feel inspired when realizing that you are sharing the same trail with hundreds of hikers along the entire Eastern Seaboard, some of whom are making the journey of a lifetime hiking the trail in its entirety from Georgia to Maine.

We made a right turn onto the AT and prepared for our approach to the summit. Here, the trail opens up and you begin to see the visual rewards for your hard work. About a quarter mile in, we emerged from the trees to discover a rock-ledge plateau offering breathtaking 360 degree views of the valley below. At roughly 2,000 feet in elevation, the clearing gives hikers a chance to gather themselves for a few minutes while taking in the beautiful scenery. Well above the tree line, it also serves as the perfect staging area for picture taking, as photographers are treated to unimpeded sightlines of lush green rolling hills brightened by pink mountain laurels sprinkled all around.

Reinvigorated, we returned our focus to reaching the summit. As we scrambled up a rocky trail, the next half mile uncovered several small openings, each revealing individual selections from the panoramic portrait awaiting us at the top. Shortly thereafter we reached our goal and arrived at the summit.

Upon our arrival we were greeted by the remnants of a tower that once stood tall at the top of the mountain. Over the past several decades, the mighty tower has been reduced to a mere pile of rocks, one that several hikers now sat atop, eating their lunch and enjoying the scenery.

We followed suit, staking a claim to our position on the rubble. Anchored by an aerial view of the Twin Lakes below, we ate, relaxed, and enjoyed the unique beauty that had unfolded before our eyes. After about 30 minutes, we packed up and headed back down, the first mission on our grand adventure finally accomplished.

About the Author: Michael DiGioia lives in Connecticut and is a free-lance sports and travel writer. A lifelong resident of the Connecticut shoreline area, the tales from Michael’s New England travel experiences have been chronicled through several publications and websites.

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3. Don’t Miss these Daring Feats at Salisbury in the Litchfield Hills of Connecticut
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