Plan my East Coast long weekend
May 13, 2022 1:31 PM   Subscribe

I will be in Simsbury, CT in late July for a wedding. My boyfriend and I want to add on a few extra days but we both have zero familiarity with the area and no constraints other than the wedding itself. We're open to staying in CT or going somewhere else via train or rental car. All this is making it hard hard to even start planning when I don't know what I'm looking for. Any suggestions or recommendations? Specifics inside.

So far the only idea we've tossed around is flying into NYC, spending a few days there, and then taking the train to the wedding and flying home from there. But I am a bit down on that idea because we've both been there a lot, it'll be stupid hot in high summer, and NYC is always a lot of walking when we are both feeling decidedly low-key right now with a preference for lounging rather than sightseeing. We also thought about the Jersey Shore but again, not enough familiarity to know where to start or if that would be a fit.

Preferences: good food, nice views or scenery, open to seeing a few attractions if they're absolutely can't-miss but otherwise a strong preference for late mornings and slow relaxed days rather than nonstop action. Ocean views/beach access would be a huge bonus. I've read good things about Mystic, is that still true? Anywhere else in CT or adjacent you'd recommend we crash for a few chill days?

Thank you for any guidance you can provide.
posted by anderjen to Travel & Transportation around Connecticut (10 answers total) 2 users marked this as a favorite
I like Rhode Island. You could go to Newport (famous for the summer mansions, but it's pretty), Narragansett, Block Island. I haven't been in ... lots of years.
posted by vunder at 1:42 PM on May 13, 2022

Wadsworth Atheneum is a cool museum worth a drive. Jacob's Pillow looks to be about an hour drive.
posted by sammyo at 2:05 PM on May 13, 2022 [1 favorite]

Blue Back Square in West Hartford is nice. Some good places to eat. I probably wouldn't spend an entire weekend there, but it would be a good afternoon.

You'll probably also get a bunch of recommendations for the Northampton/Amherst, MA area. I've only driven through, but MeFites seem to like it. Depending on where you're flying from, flying into BDL would probably be easier than any of the New York airports, and that would also be convenient to spending most of your weekend in Mass.

I also like Rhode Island and that would be fun, but it's kind of far from the part of Connecticut you're in.
posted by kevinbelt at 2:43 PM on May 13, 2022

Go tubing on the Farmington River. Get dinner and drinks in West Hartford Center. If you’re into hiking, there is plenty there, and that will also be the season for farmers markets and stuff. CT has a wine trail, but all the ciders and fruit based alcoholic beverages are better. Mystic is cool. Boston is also close.
posted by slateyness at 2:46 PM on May 13, 2022 [1 favorite]

Easiest: Mystic is a cute town, lots to do in a small area and very low-key. If you end up doing that, wander around mystic village, check out the aquarium, and maybe see if any ships are doing tours.

Intermediate: My first choice would be Cape Cod, one of the best places in the world. It's a bit more of a drive, but it's worth it. Depending on budget, you could probably find an Airbnb right on the shore or bay and have the beach super accessible. There's tons to do if you want to, but also it doesn't feel like a waste of a trip to just lounge around on the beach all day. If you end up picking Cape Cod, feel free to memail me and I can give you lots of suggestions!

Harder: Finally, this may be too much, but you could also check out one of the islands for a truly low-key destination. Block Island, Nantucket or Martha's Vineyard, or Port Jeff (not an island but you take a ferry over from CT). I say this may be too much because its a whole ferry ride to arrange, but I'm mentioning it because maybe the ferry ride is a fun excursion that you might enjoy.

(If you end up choosing inland instead of beach, definitely echoing recommendations for either pioneer valley - Northampton/Amherst or the Berkshires, also some of the best places in the world. Memail me for suggestions there, too!)
posted by carlypennylane at 5:07 PM on May 13, 2022 [1 favorite]

If you want to be at the shore w/o too much driving, then the charming Stonington CT area might be a place to base yourselves. From there you can get to Mystic, lobster shacks, etc. Getting up to RI can be a bit of driving hell on a weekend.

If you want to base yourself around Simsbury, then plan a Hartford day at the first-rate Wadsworth Atheneum and the Mark Twain house. You can find some nice day hikes in state parks around Simsbury area for a second day. Blue Back Square in West Hartford, IMO, is kind of an outdoor high class suburban mall--CB2, West Elm, et al, though I believe some decent restaurants are there.

Weekend traffic on I-95 (shore interestate) and I-91 is bad. Decide how much driving you want to do to get to your location. Simsbury is fairly close to Bradley Airport if saving time for airport travel matters.
posted by Elsie at 5:20 PM on May 13, 2022

Connecticut summer is hot and humid, so if your ambitions are low key, there’s plenty to do that won’t strain a budget or break too much sweat. If you want to keep it really local (i.e. radius of 20 miles), I’d suggest booking an AirBnB in the Farmington Valley area (Simsbury, Avon, Canton, Granby, Farmington) and flying in and out of Bradley airport. You’ll need to rent a car since public transport outside of the cities is lacking.

The pleasures of CT are decidedly not flashy, but I love them for their quiet beauty. For art, suggestions of the Wadsworth Museum, the New Britain Museum of American Art, and the Hill-Stead are excellent, for culture the Mark Twain House and Harriet Beecher Stowe House are quite interesting. The Old Newgate Prison in East Granby is a tiny historic park, but buckwild!

For dining I highly recommend the delicious and beautiful Millwright’s in Simsbury, and West Hartford center has many delightful restaurants.

For outdoor activities, nature in CT is subtle but abundant. A day tubing on the Farmington River in Satan’s Kingdom is kickass, do bring long sleeves and ratty sneakers and be prepared for horseflies!

Renting kayaks for the afternoon in Collinsville and a trip to the Collinsville Antiques Company is a lovely gentle day. Hiking the Heublein Tower trail in Simsbury is not strenuous and has scenic views, and Barkhamsted/Riverton also offer peaceful forest hikes.

Further afield, Litchfield County offers nice driving roads and antiques and hidden gem restaurants and farms tucked in the woods. If wine and cheese is your thing, I can heartily recommend a trip down to Colchester to Cato Corner Farm, one of the earliest and renowned artisanal cheesemakers in the game, and stop in at Priam Vineyards down the road for Connecticut wine that Niles Crane would probably have some opinions on.

Mystic, CT, Newport, RI, and Northampton, MA are indeed all great to visit, but if you don’t feel like spending too much time in the car getting there (between 1-2 hours each way), the deep cuts of central Connecticut are easily accessible, and in my opinion, deeply pleasant!
posted by Queen of Spreadable Fats at 5:19 AM on May 14, 2022 [2 favorites]

I live in the Northampton/Amherst MA area and there's not a lot to do here in the summer. This is a college town area and it kinda goes dead in the summer. I mean, it's pretty and I love it, but activities definitely dwindle. Although you can still go to the Emily Dickinson museum and the Eric Carle museum.

You might consider the Berkshires, though. Lennox is very nice and ramps up with Tanglewood in the summer.

Other things at random in the general area:
Mystic Connecticut
Old Sturbridge Village
Hancock Shaker Village
posted by plinth at 5:26 AM on May 14, 2022

Along with the Mark Twain House and the Wadsworth Atheneum, a Hartford day also should include a visit to the Isham-Terry house. You will need to make tour reservations ahead of time, but this minor inconvenience is worth it as our guide was one of the best house tour guides I've ever met.

Historic Wethersfield is fun if you are into historical houses and old gravestones.
posted by marguerite at 5:27 AM on May 14, 2022 [2 favorites]

Central Connecticut is a nice place to live, but not a tourist destination. Previous answers have pointed out some of the good spots to visit.

I came in to point out that Simsbury is also pretty central to all of southern New England, two or three hours from Boston, Providence, and New York City. To the west and north are opportunities for hiking, camping, and swimming in lakes. Also the eastern version of mountain climbing at Mt Greylock (drive to the top).
posted by SemiSalt at 5:37 AM on May 14, 2022

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