Unofficial Orientation Series 2019: Middletown Outings

This is an update of wilk‘s update of his previous post!



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.

And if you’re really bold and somehow have an abundance of time before finals arrive, there’s some cool shit beyond the local area too.  Here’s the 2019 Outing guide, advice from a Connecticut local. 


A quick reminder that you can check out our welcome post here and past years’ series here.

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:

  • Nature bruh: Stroll down to Harbor Park to see the Connecticut river;  Wadsworth Falls State Park is a good lil hike 3 miles from campus, with a parking lot in Rockwall for walk-up access to “Big Falls”; Mount Higby is on the Mattabassett Trail and is only a 5 minute drive from campus
  • Antique shops: Middletown is an old place, so there are a lot of antique shops, okay? We’ve got the “Amazing Everything Store and Wild Bill’s Nostalgia Store, among many other small shops
  • Bars: Middletown has a semi-robust bar scene, especially during the warmer months. Popular spots for Wesleyan Students include La BocaMezzo, and Eli Cannon’s
  • Breweries: Stroll (drive/lyft) over to the North End and you’ll find Whey Station’s occasional parking space near Middletown’s two breweries: Forest City Brewing and Stubborn Beauty Brewing Company.
  • Oddities: Just a few interesting places to explore around include Wadsworth MansionCreepy river tunnelThe dump, and Indian Hill Cemetery
  • Your daily vices: The two major liquor stores in town are Metro Spirits and Forest City Wine & Spirits; also you can stock up on your papers and such at Smoke 911
  • Recreation (take your parents here)Metro Movies, the local movie theater; the North End Farmer’s MarketAdventure Rooms, an escape-the-room establishment; The Buttonwood Tree, a performance space; MAC650, a local gallery and performance space.
    • Editor’s Note: In previous versions of this post, you’ll see The Board Room listed here. Wesleying was made aware that the owner of the Board Room, Tenzin Masselli, was convicted of sexually assaulting a classmate while a student at Wesleyan (CW for sexual assault in these linked articles: x, x, x) which is why we have removed this establishment from our list of recommendations. If you’re looking for a place to play board games in town, the Hop Knot and Klekolo both have a few stacks of board games at no extra cost to customers.


Brownstone Quarry Cliff Jumping in Portland

Beyond Middletown

Middletown has the benefit of good highway access. Sure, there’s a crap ton of traffic on Route 9 at rush hour, but otherwise, we’re about halfway between Hartford and New Haven.  Hartford is about 25-30 minutes north on I-91, and New Haven is 30 minutes south. Just over the Arrigoni bridge, you’ll hit this mysterious land that Connecticut residents call “east of the river” (Portland, Glastonbury, etc.)  To our west is Meriden, Cheshire, and Waterbury. You’ll see Cromwell, Berlin, New Britain, and Newington before heading north to Hartford. And southward, you’ll find Durham, Killingworth, East Haddam, woods, fields, and forests. (Head this way if you like cows, horses and getting lost on empty roads surrounded by lots of trees.) Small as this state is, there’s a lot you can go see.


Nightlife is almost always 21 and over, so if you’re ready for it, your best bet is in either Hartford or New Haven. 

Hartford Nightlife:  There are a few places in Hartford, but I’d recommend the Russian Lady or for some Spanish dancing, head to Casona.  Trinity is in Hartford too–but don’t do that.

New Haven Nightlife:  You’ll find a lot going on in New Haven. Check out Toad’s Place and Café Nine.  And there’s always Yale.

Oh, and local LGBTQ folks will tell you that New Haven has a stronger LGBTQ community than Hartford does, but you’ll find events and LGBTQ nightlife in both cities. Check out the drag shows at Chez Est in Hartford, and as for New Haven, try 168 York Street Café. Google says they have “theme nights”; take this as you will. You’ll find Partners Café performing similar shenanigans in New Haven, too.

Less-local coffee and restaurants:

  • Cheshire Coffee (Cheshire) – After hitting up Middletown’s Klekolo, check out some other CT local coffee joints. This one’s got great sandwiches.
  • Koffee? (New Haven) – Coffee by day, liquor by night. Have fun.
  • Tisane (West Hartford) – Lots of tea, alcohol and these things they call “mar-tea-nis”.  Some LGBTQ nightlife, too. Be sure to check out their restaurant menu.
  • Claire’s Corner Copia (New Haven) –  Sandwiches to die for. Okay, well, you won’t actually die, but they’re good.
  • Frank Pepe’s Pizzeria (New Haven) – New Haven Pizza, the trend-setter.
  • J. Timothy’s Taverne (Plainville) – Well-known for its wings.
  • Firebox (Hartford) – just go.
  • 21 Oak (Manchester) – A vegan restaurant outside of Middletown? Yes, please.  Double-check their hours before you go.
  • Need more vegan?  Pure Alchemy Juice Bar (Wallingford) is pretty good too.
  • Would you rather completely not vegan? Head to Capitol Lunch (New Britain). It’s a hotdog place, and you’ll get looks if you go in for a salad. But it’s all about the famous sauce. People fight for this shit.


The three “Hartford” Breweries: Hog RiverThomas Hooker (Bloomfield), and Hanging Hills (Hartford). And then there’s Still Hill (Rocky Hill). If you feel like straying away from I-91, check out Witchdoctor Brewery (Southington).  

Hiking/ Outdoors:

Close by:

Giuffrida Park in Meriden

  • Miller’s pond, local swimming hole
  • Cotton Hollow, Glastonbury.  another nice swimming destination
  • Sleeping Giant, a great hike if you want to do something different down by New Haven… That is, whenever they open it back up. Tornadoes are no joke.
  • Brownstone Quarries, just across the river in Portland; You can zip line, rock climb, cliff jump and wakeboard here.  It’s a national historic landmark, too.
  • A missile silo
  • Another missile silo
  • Seriously, if you’re into the missile silo thing, here.
  • Seven Falls State Park, a nice state park just down CT-9
  • Ragged Mountain, another great hike with lots of scenic views.
  • Talcott Mountain, a great place for sunset hikes; get there a little earlier to climb the tower and have a view of downtown Hartford in the distance
  • Hurd State Park, a large park in Haddam that has some nice trails along the banks of the CT River
  • Castle Craig, at Hubbard Park, where P.J. Quigley and others roasted some damn fine clams in October of 1900. You can hike up to the castle any time of year, but the road is only open from May till October, and that road closes at 4:45. This park is also known for its views and its daffodils—great for photo-ops sometime after spring break.
  • Giuffrida Park, also in Meriden. Here, you’ll find Crescent Lake, some rocks to climb, and Chauncey Peak.
  • Eagle Landing State Park, in Haddam, a great spot for hiking and eagle-watching.
  • Devil’s Hopyard, over in East Haddam. Supposedly named for some guy named Dibble and his dreams of owning a brewery, this is a good hike on the river with some waterfalls, and other cool nature-y things.

Longer drive:

Satan’s Kingdom, Farmington River Tubing in New Hartford

  • Gillette Castle, on the Connecticut River, somewhere between East Haddam and Lyme, a museum with hiking trails, a picnic area and some Connecticut history.  The castle was designed by William Gillette, a playwright known for his work with Arthur Conan Doyle and Sherlock Holmes. Part of the Connecticut Art Trail.
  • Satan’s Kingdom –uh, whitewater rafting, anyone?  Well, you’d be tubing and not rafting. It’s about an hour drive, and cash only, with some quaint restaurants across the street from the entrance. But if you want to try something different, this might be your spot. 
  • Indian Council Caves, Barkhamsted.  More like a bunch of boulders than a cave, but it’s a decent hike, and rumor has it people still find artifacts in the area.  Great trail. Long a$$ drive.
  • Litchfield Hills – It’s a long drive—absurdly long—but scenic. Download your GPS map.  Litchfield county has some great antique shops and small art galleries, as well as one of New England’s most famous creameries, Arethusa Dairy Farm. If you want to try their homemade ice cream, but aren’t up for the hour-and-a-half drive, they have a smaller shop in New Haven.  Kent Falls is up that way, too.  
  • Rocky Neck Beach and Hammonasset Beach are two of the more-popular beaches closest to Middletown.  Ocean Beach Park is a good one, too, but a bit further away.

If you’d rather hike in Middletown, there’s a trail guide for that.


Wildcat, the historic rollercoaster at Lake Compounce in Bristol

Connecticut Theme Parks:

  • Lake Compounce Theme Park, in Bristol, about 30 minutes away. They’ve got a water park, not to mention a few roller coasters: a wooden one among the oldest in the country, some superhero coasters, and one thrill ride takes you up the mountain. They’re open during Halloween too.  
  • While we’re on Halloween, check out the Trail of Terror if you get the chance.  Volunteers suit up every year to scare folks for a good cause, in the woods of Wallingford, which is about 30 minutes from campus. Tickets typically sell out. Opens September 29.  




New Haven:

    • Peabody Museum. Mostly, it’s a bunch of gigantic bones that resemble ancient animal bodies. Worth a look.  There’s other museums at Yale too.


Other nearby:

    • New Britain Museum of American Art.  New Britain, “the Hardware City” is just 20 minutes up route 9.  This museum boasts a spectacular September 11 piece, and the artist occasionally gives a talk on it during September. Free entry on Saturday mornings. While you’re in New Britain, visit “Little Poland” (Broad Street) for some authentic Polish cuisine.  
    • The Hill Stead Museum in Farmington. Historic building. They have art. If you’re here over the summer, their Sunken Garden Poetry Festival is worth checking out.


  • Mystic Seaport.  Fish. Sharks. Dolphins. Manatees. Butterflies. 
  • Mashantucket Pequot Museum. And while you’re driving down in Pequot (and/or Mohegan) territory, the casinos are hard to miss.
  • The Warrens Occult Museum. (Currently closed). Ed & Lorraine Warren’s ghostbusting work inspired several films, such as The Conjuring and A Haunting in Connecticut. Formerly in Monroe. They’re currently seeking a new location; keep an eye on their website for updates.

Other Connecticut oddities:

  • Play with goats, in pajamas. Don’t ask why, just do it.
  • The Holy Land, an abandoned Christian theme park. You’ll be trespassing if you go here. Even so, if you ever find yourself stuck in Waterbury traffic on 84, G-d help you.
  • Brain museum.  Yep.  A bunch of brains in jars, if you’re into that kind of thing.  You’ll find it in the basement of Yale’s medical library.
  • The Book Barn, a wonderful lil book shop in Niantic, where the cats roam freely.
  • 50 Cent’s (and Mike Tyson’s) old mansion.  A really big house. You seen one, you seen em all. It always seems to be for sale. Don’t buy this thing.


Lastly, September-October is fair season in Connecticut. We’ve got a lot of country fairs happening, and some of them bring in some interesting headliners.  The closest ones are the Durham Fair, Berlin Fair, Portland Fair and the Guilford Fair. Lots of interesting things to see:  tractor pulls, livestock, people who exist outside of Middletown, etc.

And though it happens in Massachusetts, if you’re not from New England, you can get a taste of this place during September at the Big E. It’s a pretty big deal.

Oh, and if you’d like to see what some (former) theater majors do in their spare time, or perhaps make use of the Wesleyan Costume Shop, the Connecticut Renaissance Faire is open on the weekends from September 1 through October 14 this year. It’s happening in Lebanon, and it’s almost an hour away from campus, but if you have the time, it’s a lot of fun.


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, but it will also 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, or outside it, 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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