Hiking the Hidden Trails: Day Trips from Stamford to Connecticut's Highlands

First things first – let's talk transport, which happens to be my specialty. If you're coming from New York City like many weekend warriors, the Metro-North Railroad from Grand Central to Stamford is your best mate. About $20 round-trip off-peak, and trains run like clockwork – nothing like the nightmare schedules I dealt with driving Route 86 through Liverpool's rain-soaked streets.

Once in Stamford, you've got options. The local bus system is decent enough (trust me, I've seen the worst of 'em worldwide), but for reaching trailheads, you might want the flexibility of a rental. I've found that car sharing often beats traditional rental companies for weekend rates. Just book ahead during peak foliage season when every city slicker wants a glimpse of those reds and golds.

If you're staying overnight, position yourself near the downtown. The hiking daypack I've carried from the Andes to the Alps has been perfect for these Connecticut jaunts – enough room for water, snacks, and layers without feeling like you're hauling a bus engine on your back.

Just a 15-minute drive northeast of Stamford lies Mianus River Park – 391 acres of proper woodland that straddles the Greenwich-Stamford border. Don't let its modest elevation fool you; what it lacks in Alpine drama it makes up for in accessibility and autumn splendor.

The Red-White-Red trail loop (about 4 miles) gives you the best bang for your buck, following the river before climbing to some decent viewpoints. Reminds me a bit of the gentler walks in New Zealand's North Island, minus the Hobbit houses. The terrain varies enough to keep it interesting without requiring the trekking poles I normally swear by on more serious hikes.

What makes Mianus special is how quickly you feel removed from civilization. Ten minutes in, and the only sounds are rustling leaves and the river's gentle burble. Beats the constant horn-honking I endured driving through Sydney's CBD for fifteen years. The park gets busy on perfect autumn weekends, so arrive early – a habit I picked up from decades of pre-dawn bus shifts.

If you've got wheels and don't mind a 30-minute drive from Stamford, Devil's Den Preserve in Weston is the business. At 1,756 acres, it's the largest nature preserve in Fairfield County and reminds me a bit of the quieter corners of Scotland's Trossachs (minus the midges, thank heavens).

The Laurel Trail to Ambler Gorge creates a satisfying 7-mile loop with just enough elevation change (about 500 feet) to remind your legs they're working. The terrain gets properly rocky in spots – I've been glad for my hiking boots that have seen me through Vietnam's mountains and Peru's pre-Incan trails.

What I love about Devil's Den is the variety. You've got babbling brooks, moss-covered boulders that look transported from some fairy tale, and proper lookout points where you can see clear to Long Island Sound on a good day. Reminds me why I started this blogging lark in the first place – to share these accessible wonders that don't require a trust fund to enjoy.

Pack a proper lunch and make a day of it. There's a brilliant spot near Godfrey Pond where you can spread out a simple picnic. Just remember to bring a water filter if you're planning to refill from streams – learned that lesson the hard way in Nepal.

After decades of watching passengers board my bus unprepared for Liverpool's notorious weather changes, I've become something of an expert on dressing for the unpredictable. Connecticut's autumn can deliver four seasons in a day – much like New Zealand, where I once hiked through sunshine, wind, and snow in a single afternoon.

Layers are your salvation. Start with a moisture-wicking base (none of that cotton nonsense that stays damp for hours), add a decent fleece, and top with a packable rain jacket that can handle sudden showers without weighing you down. When the temperature drops as sunset approaches – and it drops quickly in these hills – you'll thank me for suggesting a lightweight down jacket that compresses to nothing in your pack.

Foot care is non-negotiable. Nothing ruins a walk faster than blisters – except maybe a broken-down bus in rush hour Sydney traffic. Proper hiking socks with merino wool have served me well from the Milford Track to Vietnam's northern provinces. And always, always carry more water than you think you'll need – these Connecticut trails can be deceptively demanding.

There's something about mountain air that sharpens the appetite something fierce. After a solid day's hiking, I'm usually ready to eat the proverbial horse – a feeling familiar to anyone who's trekked the Annapurna Circuit or Scotland's West Highland Way.

Stamford's got plenty of fancy eateries where you can drop a week's wages on dinner, but that's not my style. For post-hike refueling that won't require a second mortgage, head to Colony Grill for their thin-crust pizza with hot oil (a Connecticut specialty that'll put hairs on your chest) or Bull's Head Diner for proper portions at proper prices.

If you're still on the trails as afternoon wears on, you'll want portable energy that doesn't weigh you down or crumble to dust in your pack. I've tried every energy bar known to mankind on mountains across six continents, and nothing beats the simple combination of trail mix, dried fruit, and a few squares of dark chocolate. For longer hikes, I pack a vacuum insulated food jar with homemade stew or chili – hot food halfway through a chilly autumn hike feels like winning the lottery.

Don't forget to sample some local apple cider – the non-alcoholic kind during your hike (save the hard stuff for after). Connecticut's orchards produce some brilliant cider that'll give you a proper energy boost without the sugar crash of those fluorescent sports drinks.