Labor Day comes late this year—September 7, the latest date it can possibly fall—which makes the last summer weekend feel a bit out of place. By then, school has started and lots of us will be back to the grind.
But, the calendar insists that we have one more three-day weekend. And so we must.
If you’re inspired, we scouted five nearby Connecticut escapes that can still be booked.
Glamp in East Haddam - ~$347/night
Book on VRBO
For the camping experience without the troublesome bits, you might choose one of 45 tiny black cabins scattered through the woods near Machimoodus State Park. Inside, things are pretty minimalist: a bed, kitchenette and shower; outside, a patio, firepit and trees. Some cabins sleep two and others four, and they say dogs are welcome. It's also close enough to civilization that you can spend the afternoon hiking and theoretically be at the Goodspeed Opera House’s next performance of The Snow Goose 10 minutes later.
Country Cottage in Newtown - $391/night
Book on VRBO
This cottage sits on a six-acre estate dating to 1759, surrounded by gardens and unusual trees. There's a big fireplace inside, a sunroom with a Peloton and yoga mats, and a private patio outside. The swimming pool and pickleball court are shared with the property owner, which seems like a reasonable trade for getting the run of somebody else's miniature country estate for the weekend. The Housatonic River is close by with plenty of hiking and biking trails in the vicinity.
A-Frame in Middletown - $733/night
Book on AirBnB
About a half-hour from New Haven, this hilltop A-frame is close—and hopefully far enough to feel like a vacation. With a steep roofline, walls of glass, a broad deck and a circular fireplace at the center of the main room, it’s an instagrammer’s inspiration. Downtown Middletown is just a few minutes away, so dinner on Main Street is as easy as hanging out in the trees.
Lodge in Killingworth - ~$705/night
Book on VRBO
This five-bedroom lodge in Killingworth sits on 24 wooded acres beside Chatfield Hollow State Park. The house is a mix of heavy timber, exposed brick and midcentury furniture, with vaulted ceilings, big windows and several long, low living spaces. Outside, there are patios, an outdoor kitchen and enough land that you hopefully feel like you’ve really gotten away.
Cabin in Madison - $245/night
Book on AirBnB
You could travel further, but it's hard to argue with a cabin on the Neck River 30 minutes from New Haven. This rental looks rustic with wood-paneled walls, old furniture, and a stone porch. The place comes with kayaks and paddleboards for exploring the river and the host promises the adventurous and confident can paddle all the way to Long Island Sound. Downtown Madison and its beaches, bookstore, movie theater and restaurants are a short drive away.
Written by Daily Nutmeg Staff.
