Connecticut Outdoor Challenge List

PRELIMINARY Connecticut Outdoor Challenge List

Help me fill in the blanks! Or change it up to make it better! Just email me or leave comments here or on the social media that brought you here. I’ll put links in later to explain some of the stuff better. I’m looking for more stuff in southern and eastern Connecticut too. Thanks.

This 50-item challenge is no joke, but I encourage everyone to go for it. Take your time. Enjoy Connecticut. Bring your camera.

SH = Shorter hike
LH = Longer hike
$ = may have a fee
$$ = definitely has a fee

The Challenge rules
Hike Smart, Hike Safe

I will not bother linking information about each challenge item, as that will be up to you to research and plan on your own. (For me, that’s half the fun.) I will link my own experiences though, because that’s what you expect.


5 Long Hikes/Trails

CT section of the Appalachian Trail, including at least one overnight (52 miles)
CT section of the New England Scenic Trail (131 miles), comprised of:

Metacomet Trail (63 miles)
Mattabesett Trail (52 miles)
Menunkatuck Trail (16 miles)

These three established hiker challenges “require” you to pay a fee to the organizations that maintain the lands, trails, and programs. You don’t have to, of course, but then you won’t have the official completion items from the organizations and you won’t be helping their noble causes.

Become a Sleeping Giant Master, Hamden (~40 miles) $$
Complete the Steep Rock Hiker Challenge, Washington (~40 miles) $$
Complete the Burlington Trail Master Program, Burlington (~40 miles) $$

5 Other Hikes

Highest point in Connecticut (Mt. Frissell) and CT-MA-NY Tri-point, Salisbury
CT-MA-RI Tri-point, Thompson

5 Waterfalls

Enders Falls, Granby
Falls Brook Falls, Hartland, H
Roaring Brook Falls, Cheshire, H
Blackledge Falls, Glastonbury, H
Nonnewaug Falls, Woodbury H

5 Towers

You must ascend to the top!

Heublein Tower, Simsbury, H
Soapstone Mountain Tower, Somers
Haystack Mountain Tower, Norfolk
Mt. Tom Tower, Litchfield, $ H
Orenaug Park Fire Tower, Woodbury, H

5 Other Cool Things

Gillette’s Train Tunnel, East Haddam, H
“Air Tunnel” over the West Rock/Heroes’ Tunnel, New Haven, H
Cedar Hill Cemetery Tour, $ H

5 Ingestible Things

Eat on a stump at The Place, Guilford, $$
Drink a sour beer at OEC Brewery’s patio, Oxford, $$ (they sell non-alcoholic beer)
Enjoy wine at any CT winery outside, $$ (can sub-in a cidery)
Enjoy We-Lik-It Ice Cream, Pomfret, $$
Attend a Farmer’s Cow Open Farm (I strongly suggest Cushman Farm in Franklin – roasted corn!)

5 Living Things

Cathedral Pines, Cornwall, H
Largest (Pinchot Sycamore) and Coolest (Granby Oak) Trees in Connecticut, Simsbury/Granby
Observe bald eagles at Shepaug Dam, Southbury
Go to a cheese-maker, buy cheese, and take a picture with a cow or goat there $$

5 Wet Things

Walk the tombolo out to Charles Island, Milford, $
Swim in a lake, (I strongly suggest Lake Waramaug in Kent) $
Dip your toes in Diana’s Pool, Chaplin
Cliff-jump at Brownstone Park, Portland $$
Kayak or canoe to at least 1 Thimble Island, Branford

5 Rocky Things

Mary’s Rock, Granby, H
Take a picture with Frog Rock, Eastford
Climb to top of The Brethren, Hamden
Wolf Den, Pomfret, H
Judges Cave, New Haven, H

5 Random Things

Go apple picking somewhere, $$
Tailgate at a UConn football game or Run a 5K, $$
Walk on ancient sand dunes, Mattianuck State Preserve, Windsor, H
Attend an i-Park Open House, East Haddam, H
Wildcard – do something cool not on this list and explain why it should be on this list

The Last Thing

Enjoy a drink outside on my patio, collect your certificate, tour of the CTMQ headquarters, and discuss your journey, West Hartford

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