Six Weekend Getaways for the Summer

I love New Haven with all of my heart and a little bit of yours. But during the dead heat of summer, I can forgive people for looking outward to Greater New England and beyond to search for that perfect weekend getaway. Especially in the sorta-post-COVID era, where we desperately want to get out of the house, but maybe aren’t ready to spend a month in Portugal or Egypt.

Sometimes you just gotta get outta town. While I’ve covered beaches in the past, I wanted to take a moment to offer some more significant getaways. These are all doable as a weekend getaway, though if you wanted to spend 3-4 days, that wouldn’t hurt, either.

Block Island

I’d never been to Block Island before I was 30 years old, but it’s now turned into an annual trip with my friends. Each year we rent a house and spend anywhere from a weekend to a full week on the Island. You can take a ferry from New London or Point Judith, Rhode Island.

Timothy J. Quill, CC BY-SA 4.0, via Wikimedia Commons

Block Island, like Cape Cod, perfectly captures that kind of old timey New England aesthetic, with white-and-gray buildings, seafood shacks and ice cream shops, souvenir shops and bars and restaurants. Also, Ballard’s, which is a huge beach bar, is the only place I’ve ever seen a couple have intercourse in broad daylight on a beach. So that’s something.

(Note: 4th of July Weekend is a hot mess on Ballard’s.)

Still, Block Island has a lot of natural beauty and is a great place to bicycle or moped around or enjoy the Bluffs. (Note: I swear Block Island has the highest per-capita first-time moped users on the planet.)

Plus, they have some of the best mudslides, which makes day drinking feel like a fun dessert.

Appalachian Trail Backpacking

In the Northwestern corner of Connecticut is the quaint town of Salisbury, population: 3598.

In this town is the Lion’s Head Trail, which actually connects to a lil’ old trail you might have heard of called the Appalachian Trail. The AT, as the cool kids call it, runs over 2,000 miles from Georgia to Maine, and crosses, very briefly, into our fair state in the Northwestern Corner.

While the idea of a full week of backpacking can be daunting, an overnight trip up to the Appalachian Trail is the perfect way to escape the city and just try it out for a night. And if you play your cards (and food) right, you might not even have to poop in the woods.

Once you hit the AT, there are several camping sites nearby you can stay overnight, including a couple of shelters (wooded/rooved structures above the ground). Beautiful views of Connecticut and New York, as well as the gorgeous night sky and total silence of the absence of civilization are truly sights and sounds to behold.


There is something absolutely visceral about carrying everything you need to survive in this world on your back. Everyone who is able should try it at least once. Plus, it’s free! Just clean up after yourself!

Newport, Rhode Island

People often view Connecticut as a fancy-pants state where everyone wears boat shoes and salmon shorts and has a collar and whatnot.

Newport, Rhode Island is that imaginary place.

MVASCO, CC BY-SA 3.0, via Wikimedia Commons

Home to a bevy of enormous, historic mansions, eateries, beaches, and various shops and restaurants, Newport is a destination for people all over New England. Especially if you’re looking to party.

The Cliff Walk is an especially popular destination, and I myself have vomited in some of the classiest bathrooms Newport has to offer. Another fun activity is driving around and checking out the mansions and trying to figure out how rich the people are and which part of their body you would eat first.


The Catskills are an underrated gem of the tri-state area. While not technically New England, you can get to many of the popular towns like Woodstock and Phoenecia in two or two-and-a-half hours.

The Catskills are kind of a catch-all for mid-state New York, with the Catskills Mountains and lots of adorable and beautiful hotels and AirBnB options. Plus fantastic hiking, wide-open skies, and small-town folks who you will desperately avoid discussing politics with.

Gamweb, CC BY-SA 3.0, via Wikimedia Commons

You don’t realize how much light pollution affects your life until you stare up at the stars from the Catskills and take in the majesty of the night sky and think about how small you are and how little time you have on this Earth to tip your local blogger.

Mystic, Connecticut

“Hey, you should check out New London,” said nobody since the 19th century.

Yet nestled in the New London area is Old Mystic, with its quaint downtown full of restaurants and ice cream shoppes and adorable AirBnB’s and hotels. Did I mention the ice cream? (Seriously, there’s an ice cream shop downtown that people wait in line for Pepe’s-style.)

peasap, CC BY 2.0, via Wikimedia Commons

Also, Mystic Pizza is inexplicably still open? You might think it’s insane that a pizza restaurant could ride the high of a 1988 Julia Roberts film into permanent cult status but here we are. Remember when Mystic Pizza had frozen pizzas you could buy at a grocery store? Man, the 90’s were nuts.

Anyway, Mystic is a great little mini-getaway only an hour from New Haven. You can walk around the downtown and riverfront area, or check out the old-timey boats in Historic Mystic Village.

Also, there’s Mystic Aquarium! Is it ethical to watch massive sharks live their entire lives in captivity? I don’t know! And at this point I really don’t want to try to figure it out.

Burlington, Vermont

I considered whether or not to include Burlington, Vermont, since it’s not exactly an easy weekend getaway. The drive from New Haven to Burlington is a full five hours. It’s practically Canada.

Yet Burlington remains one of my absolute favorite places to visit. It’s got great bars, restaurants, cafes, outdoor stores, breweries, gorgeous nature, kitschy shops, way too many places selliing “Keep Vermont Weird” t-shits which is like hey just keep smoking weed I guess.

One of my favorite stores in the world is the Outdoor Gear Exchange, which has both new and used camping and hiking and all kind of outdoor equipment. Downtown Burlington is absolutely perfect, with its pedestrian-only access and huge outdoor spaces for all the nearby restaurants and bars.

Dicky Hayward, CC BY 2.0, via Wikimedia Commons

Plus, if you’re sober like me, plenty of coffee and book and chocolate shops. Chocolate!!! Hell yeah. It’s the drugs of the drug-free world.

If you’re looking for a challenging hike, check out Camel’s Hump, about an hour south of Burlington. Take the Long Trail up and the Barrows Trail down. It’s challenging but absolutely perfect and a stunning view from the top of Vermont’s majestic Green Mountains.

North Beach Campground is a great place to stay right on the lake, though be forewarned, there’s a lot of families and kids and they really pack those sites in there so if you’re trying to party be prepared to get yelled at.

Or listen to your buddy Dave get yelled at and feel shame-by-association.

Well that’s it for this week! I hope y’all are out there having a great summer and we’ll see you back in the city soon enough. I’ll see you at Barcade, where I am absolutely destroying the Frogger machine.

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