Unofficial Orientation Series 2017: Middletown Outings

This is an update of my post from last year!


This is part of our 2017 Unofficial Orientation Series. A quick reminder that you can check out the welcome post here and past years’ series here.

Toto, we’re not in Bushwick anymore. You’ve now left the comfort of deep Brooklyn, as they call it, for the not-so-dissimilar milieu of Wesleyan. Just kidding, a vast majority of Weskids are from not-Brooklyn, not-LA, and not-Bay-Area, although it might seem otherwise.

For all of you from those (wonderful) places, and all of you from other places, Middletown is different than those places (shocking!). It was once the largest city in Connecticut, circa pre-war-of-1812. Can your hometown claim that title? Nah. Unless you’re from Middletown, in which case you are probably way more qualified than me to write this post.

While Wesleyan is fine and there is usually never a shortage of things to do on campus, Middletown and the surrounding area truly have some wonderful gems that are worth knowing about as you settle in and look for things to do other than vape on Foss. Here is wesleying’s (my) attempt at travel blogging. Bring your fanny pack:

In Town


Wadsworth Falls State Park

Middletown is a city of around 40 square miles and 50,000 people. At the center of town life is Main Street, which flanks the Connecticut River and is full of restaurants, bars, shops, and more. Nestled in the Connecticut River Valley, there are also many hiking opportunities and natural habitats to explore, both in and around town. Here are some of the things you can do in town:

Around Town

Brownstone Park cliff jumping in Portland

Brownstone Park cliff jumping in Portland

Hartford is only 25 minutes north on I-91. And New Haven only 30 minutes to the south. There are also lots of smaller towns just surrounding Middletown, such as Portland, Cromwell, Newington, and Rocky Hill that all have their own charm. Here are some things to do around Middletown:


Seriously, get the fuck off campus. It’s really healthy to give some geographical context to your Wesleyan experience. Getting off campus will not only clear your head, it will inform your academics, your activism, your newfound privilege as an (elite) college student, and your tummy. So bring your booty (monetary or bodily) around town and get invested in your new locale.

Don’t Frown

Have fun here! Taking a trip off campus is a great way to cement some friendships, make new friends, or even just to have some alone time. Once the school year gets going, do get on the Outing Club’s listserv. They plan outings for every weekend of the semester, and are super accessible and friendly.

If you have anything to add to this list, drop it in the comments or send an email to staff[at]wesleying[dot]org and we’ll try to keep this list up to date.

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