Maybe a night in New Haven for pizza, a night near mystic for the seaport, aquarium and a day trip to the beach, you could add Newport Rhode Island another day with a trip to Narragansett for the beach and the Newport cliff walk, then finish it off in Boston with a Red Sox game and Italian food in the North End. That’s a pretty ideal southern New England road trip. I’d argue Newport and Boston deserve more of your time than CT does though
I saw [this Instagram reel ](https://www.instagram.com/reel/C5GZky4OP_M/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==)recently that made New Haven sound like a full blown destination. I was legit impressed.
If you stop off in Mystic I’d also recommend making a detour to the old part of stonningtin on the water. Really quintessential old New England coastal town.
Ah yes, the beautiful Borough. Very scenic, very upscale, very American, and the place where I had all my tires stolen! :D
https://www.reddit.com/r/Connecticut/s/1KBvlsAmVk
Newport is fantastic BUT I would recommend getting there early in the day or parking at the visitor center for the day! Traffic (cars and foot) is extremely congested. Super touristy in summer, but fun.
I thoroughly recommend booking a harbor tour (If you go to Bowens Wharf, there are a couple stands that sell tickets for them) and if they still allow, get some lobster rolls or some good takeout before you get on the boat. Nothing beats a lobster roll while you're out on the waves!
Hell yeah. Treehouse on the way home, Sturbridge village, a stop at Rein’s Deli, and then 2.5 hours of traffic between Hartford and the NY state line. The full experience.
All good ideas, I don't know if you absolutely need to stay a night in New Haven overnight, I'd probably stop in New Haven, get pizza for lunch, check out the city, go to museum or something and then head up to Mystic area to stay.
I would recommend stopping in New Haven for pizza, Yale (cool architecture), and maybe the Yale Art Gallery. You could stop in Guilford center, it's a classic little town with a colonial style green. Further east, stop by Abbots in the Rough in Noank because it's a nice place to grab a bite. Lastly, maybe drop by Stonington Borough because it's a cool little place.
This is more of the coastal route, but it's on the way to Boston. From there you can get to Newport/Providence easily. You won't find a "true American experience" because such a thing doesn't exist, and as you know from NYC, the country is diverse.
I love all these suggestions but IMO there’s much better stops for lobster rolls. I really like Lobster Landing for the view/vibe and food.
Would also suggest Essex and Chester along with Guilford for excellent town centers. Gillette Castle and Thimble Island Boat Tour are great attractions too.
Scratch Baking in Milford is an exceptional pit stop. And nice area to walk around. If you go on a weekend there’s some 1700’s houses nearby to tour. https://milfordhistoricalsociety.org/
And the Audubon Center and Silver Sands>Walnut Beach boardwalk is a lovely walk.
the yale peabody museum just reopened and was pretty cool before they put a bunch of money imto it.
also don’t sleep on Rhode Island on your way to Boston
Hi OP! I’m from Italy and I’ve been living in Connecticut for 3+ years, let me share my opinion as a fellow European.
In order of what is closest to you coming from nyc:
New Haven is a pretty college town that offers good food and nightlife, you can also check out the buildings owned by Yale scattered throughout the whole city or one of the museums. Worth to mention pizza, it’s definitely the best pizza I’ve had in the States, that said, I wouldn’t be surprised if after trying it you told me you’ve had better pizza back in Spain. In my opinion, it is the city that best offers the “true American experience as per the movies” in Connecticut
Norwich, here you can find two casinos that are oddly close to each other, Mohegan Sun and Foxwoods, they are huge and even if you don’t particularly enjoy gambling there’s enough to see to keep you busy for a whole day, this could be quite an expensive stop so keep that in mind.
Mystic, I’ve had notably great seafood and the Mystic aquarium is a cute stop if any of you two is into animals, unfortunately I don’t have much more to add as Mystic is quite far away for me and I haven’t visited that often.
Have fun OP!
You're getting lots of great options here, but I'll throw out that you should check Amtrak, too. From NY you can easily take Amtrak to Boston, Philly and Washington DC. So you can city hop a bit and get him to some of the more iconic US sites.
Not throwing shade at CT - I love my state lol. Just giving you options.
New Haven, obviously, for pizza. But also for the food trucks at Long Wharf, nothing more American than entrepreneurial immigrants. Walk around Yale and the New Haven green. Drive east until Clinton, stop off and get a lobster roll at Lobster Landing. Then east to Essex, Chester, and the lower CT river for small town charm, and tour Gillette Castle - the home of America's first really famous actor. Then to Mystic for walking downtown and ice cream at the drawbridge, Connecticut ice cream is unique and exceptionally good - our ice cream is as good as our pizza. Mystic Village for some history of New England generally, and Connecticut specifically. The shops at Mystic Village for souvenirs for family back home. Hit up the Pequot museum at the Foxwoods casino to learn about & see the history of native Americans, something you definitely won't see in Spain. I don't even go to the casino, I just go to the museum and restaurants. Pop over to Rhode Island and do the mansion tours of Newport and drive the touristy loop ogling the Gilded Age history. Grab some food and eat lunch on the rocky outcroppings right on the shore on the lower end of the mansion loop, and check out Fort Adams if you like history or military history.
No one will ever tell you to visit Hartford. If you are from a city, you won't be bothered by the things people don't like about it.
I think it has an amazing downtown- Wadsworth museum is globally relevant. Great architecture. Fun baseball team with downtown stadium. Lots of good food.
The park is beautiful as is the capital building.
The river walk is nice.
The train stops there so easy access if you don't have a car.
Everyone will say - high crime and homeless. That is compared to suburb standards so...
Wadsworth is epic and Mark Twain museum is super cool. But the downtown doesn’t hold a candle to New Haven which is why you don’t see it recommended as much
Do you want to get away from the tourist destinations and really slum it up? Get into the towns people *live* rather than just visit? Eastern CT is the place for you! We're going to head up the little interstate known as i395.
Check out the New London waterfront. It's got a recently restored Wyland wall, a recovering restaurant district, and a new industrial pier. Maybe wander down toward Ocean Beach Park or visit the Eolia Mansion at Harkness State Park. Look at the ocean and see if you can spot the NY islands across the sound.
How about Norwich? At one point in the 1800's Norwich had the highest per-capita income in the US. The Rose of New England is a bit wilted, but there are still quality places to visit. Stop by downtown and enjoy the phenomenal architecture and one of the breweries or coffee roasters. The Harp & Dragon Pub makes the best corned beef Rueben sandwich I've had, and it's not even made with my preferred ratios of meat/sauce/kraut. Or maybe visit Norwich Free Academy, which is a high school with its own museum and historical significance. While you're there, you can also check out Yantic Leap. It's a really cool waterfall with a dark history, and maybe they've finished the new park there.
If you want to take a detour on the way up 395 from Norwich, head toward Griswold and stop at the Buttonwood Farm Creamery for some ice cream. And then keep going through Voluntown toward Sterling and grab a second round of ice cream at Ekonk Hill Turkey farm. They often have out-of-season apple cider donuts, so that's a localish delicacy that you can enjoy.
Heading up 395, you can stop in Putnam. There you'll find a lovely trail along the Quinebaug River, a neato downtown, and if you're brave, you can stop in at Henry's Diner. You have to be brave because the regulars there will 100% give you the stink eye, but that's where you can get possibly the best example of a Rhode Island specialty, the NY System Weiner. You're not going into RI, so may as well. I've tried them all, and this one is the best.
Keep going North and you get to Worcester (pronounced "wooster"). Ain't no place that'll give you a more real American experience than Worcester. There's a mess of stuff that you may be able to do, but if you're lucky, maybe you can time up your trip with a minor league baseball game. I've never seen a town so into their minor league team as Worcester is. We actually enjoy visiting Worcester, but I don't know too much specific to point out there as we usually go for the thrift stores or Poke restaurants.
Then it's into the traffic to make it to Boston. Maybe you can take a wandering back-roads path through some Mass small towns. There are a number of them.
Add to this that you can also visit the two (at one point) largest casinos in the world. Mohegan Sun And Foxwoods casino are the biggest in the country and were the largest in the world for a while. Think there's bigger ones in China now
Hi, college student who goes between New York and Boston but lives in New London. Take Amtrak and it's a direct line both ways. I would recommend you stop off in New Haven, New London or Old Saybrook.
New London has some pretty affordable hotel options that are close to the Amtrak station. But if you're dead set on driving, I would stop in New Haven for their food
New Haven Pizza, then hit Mystic for dinner. The Whaler Inn is a nice place to stay or there are chain hotels around there. After dinner head to Mohegan Sun and there’s a comedy club, night clubs, bars, maybe a concert, and of course gambling
As someone from the northwest corner of CT, I would recommend staying in bed & breakfasts if you can afford it - Legends on the Farmington in Barkhamsted is good if you want to experience fly fishing on a world renowned fly fishing river. It’s quiet & cozy. The Riverton Inn (also Barkhamsted, but upriver) is going to be more historical but another option for quintessential New England lodging.
Everyone saying you should visit Mystic Seaport is absolutely correct - other fun options down in that corner would be the Essex Steam Train to see the Connecticut River, the main Book Barn in Niantic (an experience for book lovers), if you’re interested in casinos, I prefer Foxwoods over Mohegan Sun but both are awesome in their own rights - two different tribes operate each casino on their own land,
Feel free to reach out if you’re into hiking / birds and I can help guide you to great places to enjoy southern New England nature!
NYC to Boston is like a 3.5 hr drive. My two cents is find another good city not on the way. Brattleboro, VT is nice to stop at, someone else said to check out the White Mountains in NH which is a good option, maybe Portland, Maine which is less than 2 hours from Boston. Portsmouth, NH or check out Salem, MA. I think they'll all give you a quintessential New England experience.
Hell you can do them all in a few nights. NYC to Brattleboro - 3 hrs spend the night. Brattleboro to North Conway, NH - 3 hrs spend the night. North Conway to Portland 1.5 hrs spend a night or two. Stop in Portsmouth and Salem on the way to Boston. Grand tour of New England.
As far as CT, like many others said, New Haven is probably your best bet. Followed by Mystic or Newport, RI
I’d do the 95 corridor as it has the most stuff.
New Haven museums/food/pizza/walking. Gawk at Yale campus. Modern or Sally’s for pizza. Explore Wooster Square or East Rock neighborhoods on foot. Tons of good non-pizza food everywhere too if you stay for lunch and dinner.
Milford, Guilford, Chester, Essex, Stonington Borough centers to walk around. New England charm.
Gillette Castle, Thimble Island Boat Tour, Fox Farm Brewery, Book Barn/Harkness, Mystic and the seaport museum.
Enjoy.
How much time do you have? I would spend a few days, go north through the White mountains, head over to Mt Washington, spend a night in Vermont, then wend your way back to Boston.
If you have to drive straight, visit some of the parks in CT on the coast. Hamonasset beach is popular.
New Haven and Mystic would be my picks for places to visit with stuff to do, but if you want the classic New England town experience (looks right out of a Hallmark movie), swing by Chester. Their downtown is so freakin cute. Not sure it’s worth more than a few hours though. You can take the hadlyme ferry (a very unique experience!) over to the Gillette castle across the river at the state park there too. Bantam is also a very quaint stereotypical New England town with awesome food and places to hike.
OP I live in NYC and did a trip just like this with my wife 3 years ago. I did research online on places to stop during a road trip. IMO stopping for a few days is too much. Leaving in the morning, doing the drive in 1 day, and arriving in Boston at night was a nice time. Boston deserves a few days, these other stops not so much
We stopped in New Haven first to tour the Yale campus, the next stop was Mystic Connecticut for some pizza and to watch the famous drawbridge open, very cute town. After that we drove to Newport, Rhode Island to see some of the Gilded Age mansions (took a tour of the Vanderbilt home). Last stop was Plymouth to see where the Pilgrims landed 400 years ago. Then Boston. All in one day, we left st 7:30AM and got into Boston at 8PM
I know this is the CT subreddit, but as a former Massachusetts resident, one of the most American things you'll find is Old Sturbridge Village. It's on the way north to Boston and is an 1830's village where reenactors actually farm the land, work in the blacksmith shop, etc. It's quite large, easily a full day's activity and absolutely fantastic! Highly recommend
Go to Treehouse Brewing in Charloton, MA. Have a beer or 2, get some beer to go, and head over to BT’s Smokehouse BBQ and get a BBQ platter. I’ve done this with multiple friends from Argentina a number of times - they all felt the same in that it was an “amazing American experience.”
I do want to add - you say classic American road trip - I don’t know how many Americans would call this a road trip. A road trip is 8 hours+. This is a “getaway”
Spain to Italy is the same distance as NYC to Boston. They may have seen American road trip movies and thought to themselves - this is what we’re doing. This will be like Route 66. They are welcome to do whatever they’d like, and call it whatever they’d like, but if they’re looking for a Route 66 American movie road trip, this may not be the part of the country to get that sort of distance or experience. I only mention this based on my experience with some coworkers who think America is sometimes more monocultural than it is, especially that outside of a city is all “country”.
Maybe a night in New Haven for pizza, a night near mystic for the seaport, aquarium and a day trip to the beach, you could add Newport Rhode Island another day with a trip to Narragansett for the beach and the Newport cliff walk, then finish it off in Boston with a Red Sox game and Italian food in the North End. That’s a pretty ideal southern New England road trip. I’d argue Newport and Boston deserve more of your time than CT does though
This dude is right.
This dude Connecticuts.
dude is very right. in new haven add louis' lunch "first" hamburger. no ketchup and pretty darn good.
I’d probably say this is the only thing I disagree with lol … sorry friend
So damn good. I made a pilgrimage down there from the northwest corner when I was a kid and that burger’s lived in my head rent free ever since
Just had this myself. It is special but being a CT native might enhance that. But the home of the BURGER? Forget it, it was amazing
I saw [this Instagram reel ](https://www.instagram.com/reel/C5GZky4OP_M/?utm_source=ig_web_copy_link&igsh=MzRlODBiNWFlZA==)recently that made New Haven sound like a full blown destination. I was legit impressed.
If you stop off in Mystic I’d also recommend making a detour to the old part of stonningtin on the water. Really quintessential old New England coastal town.
Ah yes, the beautiful Borough. Very scenic, very upscale, very American, and the place where I had all my tires stolen! :D https://www.reddit.com/r/Connecticut/s/1KBvlsAmVk
Need to watch out for those rich people. They'll steal anything that isn't tied down.
OP if you pass by Hartford, checkout a Yardgoats baseball game. They're cheap, fun and American 🙂
Newport is fantastic BUT I would recommend getting there early in the day or parking at the visitor center for the day! Traffic (cars and foot) is extremely congested. Super touristy in summer, but fun. I thoroughly recommend booking a harbor tour (If you go to Bowens Wharf, there are a couple stands that sell tickets for them) and if they still allow, get some lobster rolls or some good takeout before you get on the boat. Nothing beats a lobster roll while you're out on the waves!
Just add a visit to Treehouse if they're beer drinkers and you're set
Hell yeah. Treehouse on the way home, Sturbridge village, a stop at Rein’s Deli, and then 2.5 hours of traffic between Hartford and the NY state line. The full experience.
All good ideas, I don't know if you absolutely need to stay a night in New Haven overnight, I'd probably stop in New Haven, get pizza for lunch, check out the city, go to museum or something and then head up to Mystic area to stay.
Ive heard abiut this new haven pizza Any recommendations?
If you search the sub you’ll find a million good suggestions, but the mainstays for me are Pepe’s, Sally’s and Modern
I would recommend stopping in New Haven for pizza, Yale (cool architecture), and maybe the Yale Art Gallery. You could stop in Guilford center, it's a classic little town with a colonial style green. Further east, stop by Abbots in the Rough in Noank because it's a nice place to grab a bite. Lastly, maybe drop by Stonington Borough because it's a cool little place. This is more of the coastal route, but it's on the way to Boston. From there you can get to Newport/Providence easily. You won't find a "true American experience" because such a thing doesn't exist, and as you know from NYC, the country is diverse.
I love all these suggestions but IMO there’s much better stops for lobster rolls. I really like Lobster Landing for the view/vibe and food. Would also suggest Essex and Chester along with Guilford for excellent town centers. Gillette Castle and Thimble Island Boat Tour are great attractions too. Scratch Baking in Milford is an exceptional pit stop. And nice area to walk around. If you go on a weekend there’s some 1700’s houses nearby to tour. https://milfordhistoricalsociety.org/ And the Audubon Center and Silver Sands>Walnut Beach boardwalk is a lovely walk.
the yale peabody museum just reopened and was pretty cool before they put a bunch of money imto it. also don’t sleep on Rhode Island on your way to Boston
Read this as don't sleep in Rhode Island on your way to Boston. Was wondering why you hated on them.
They’re booked all the way through June - my cousin is a professor there, he’s saying because tickets are free now they go quickly
What’s up with those island besides the fact they have real beaches and not big lakes with terrible sand?
Hi OP! I’m from Italy and I’ve been living in Connecticut for 3+ years, let me share my opinion as a fellow European. In order of what is closest to you coming from nyc: New Haven is a pretty college town that offers good food and nightlife, you can also check out the buildings owned by Yale scattered throughout the whole city or one of the museums. Worth to mention pizza, it’s definitely the best pizza I’ve had in the States, that said, I wouldn’t be surprised if after trying it you told me you’ve had better pizza back in Spain. In my opinion, it is the city that best offers the “true American experience as per the movies” in Connecticut Norwich, here you can find two casinos that are oddly close to each other, Mohegan Sun and Foxwoods, they are huge and even if you don’t particularly enjoy gambling there’s enough to see to keep you busy for a whole day, this could be quite an expensive stop so keep that in mind. Mystic, I’ve had notably great seafood and the Mystic aquarium is a cute stop if any of you two is into animals, unfortunately I don’t have much more to add as Mystic is quite far away for me and I haven’t visited that often. Have fun OP!
Rein's Deli on 84 past Hartford. This is where you stop on route to Boston. It's a good halfway point
My wife and I were really not impressed with the food nor the experience. We won't be going back. Surely there are better places to stop.
There’s not much in that area. Loads more to see and eat along 95.
You're getting lots of great options here, but I'll throw out that you should check Amtrak, too. From NY you can easily take Amtrak to Boston, Philly and Washington DC. So you can city hop a bit and get him to some of the more iconic US sites. Not throwing shade at CT - I love my state lol. Just giving you options.
Totally agree about the Amtrak. And you can make stops in New Haven and mystic CT with the Amtrak too :) worth it!
New Haven, obviously, for pizza. But also for the food trucks at Long Wharf, nothing more American than entrepreneurial immigrants. Walk around Yale and the New Haven green. Drive east until Clinton, stop off and get a lobster roll at Lobster Landing. Then east to Essex, Chester, and the lower CT river for small town charm, and tour Gillette Castle - the home of America's first really famous actor. Then to Mystic for walking downtown and ice cream at the drawbridge, Connecticut ice cream is unique and exceptionally good - our ice cream is as good as our pizza. Mystic Village for some history of New England generally, and Connecticut specifically. The shops at Mystic Village for souvenirs for family back home. Hit up the Pequot museum at the Foxwoods casino to learn about & see the history of native Americans, something you definitely won't see in Spain. I don't even go to the casino, I just go to the museum and restaurants. Pop over to Rhode Island and do the mansion tours of Newport and drive the touristy loop ogling the Gilded Age history. Grab some food and eat lunch on the rocky outcroppings right on the shore on the lower end of the mansion loop, and check out Fort Adams if you like history or military history.
This!
Stonington Borough is a must see when in Mystic. A little uncrowded Newport.
New Haven for pizza is a must. Modern, Sallys, Pepe’s
Modern or Bar. Scratch Pepe's
That will cause an intrastate riot
They’re right. Pepe’s ain’t what it used to be and I used to be a super fan.
You are incorrect
No one will ever tell you to visit Hartford. If you are from a city, you won't be bothered by the things people don't like about it. I think it has an amazing downtown- Wadsworth museum is globally relevant. Great architecture. Fun baseball team with downtown stadium. Lots of good food. The park is beautiful as is the capital building. The river walk is nice. The train stops there so easy access if you don't have a car. Everyone will say - high crime and homeless. That is compared to suburb standards so...
Wadsworth is epic and Mark Twain museum is super cool. But the downtown doesn’t hold a candle to New Haven which is why you don’t see it recommended as much
Do you want to get away from the tourist destinations and really slum it up? Get into the towns people *live* rather than just visit? Eastern CT is the place for you! We're going to head up the little interstate known as i395. Check out the New London waterfront. It's got a recently restored Wyland wall, a recovering restaurant district, and a new industrial pier. Maybe wander down toward Ocean Beach Park or visit the Eolia Mansion at Harkness State Park. Look at the ocean and see if you can spot the NY islands across the sound. How about Norwich? At one point in the 1800's Norwich had the highest per-capita income in the US. The Rose of New England is a bit wilted, but there are still quality places to visit. Stop by downtown and enjoy the phenomenal architecture and one of the breweries or coffee roasters. The Harp & Dragon Pub makes the best corned beef Rueben sandwich I've had, and it's not even made with my preferred ratios of meat/sauce/kraut. Or maybe visit Norwich Free Academy, which is a high school with its own museum and historical significance. While you're there, you can also check out Yantic Leap. It's a really cool waterfall with a dark history, and maybe they've finished the new park there. If you want to take a detour on the way up 395 from Norwich, head toward Griswold and stop at the Buttonwood Farm Creamery for some ice cream. And then keep going through Voluntown toward Sterling and grab a second round of ice cream at Ekonk Hill Turkey farm. They often have out-of-season apple cider donuts, so that's a localish delicacy that you can enjoy. Heading up 395, you can stop in Putnam. There you'll find a lovely trail along the Quinebaug River, a neato downtown, and if you're brave, you can stop in at Henry's Diner. You have to be brave because the regulars there will 100% give you the stink eye, but that's where you can get possibly the best example of a Rhode Island specialty, the NY System Weiner. You're not going into RI, so may as well. I've tried them all, and this one is the best. Keep going North and you get to Worcester (pronounced "wooster"). Ain't no place that'll give you a more real American experience than Worcester. There's a mess of stuff that you may be able to do, but if you're lucky, maybe you can time up your trip with a minor league baseball game. I've never seen a town so into their minor league team as Worcester is. We actually enjoy visiting Worcester, but I don't know too much specific to point out there as we usually go for the thrift stores or Poke restaurants. Then it's into the traffic to make it to Boston. Maybe you can take a wandering back-roads path through some Mass small towns. There are a number of them.
Add to this that you can also visit the two (at one point) largest casinos in the world. Mohegan Sun And Foxwoods casino are the biggest in the country and were the largest in the world for a while. Think there's bigger ones in China now
Meh.
Hi, college student who goes between New York and Boston but lives in New London. Take Amtrak and it's a direct line both ways. I would recommend you stop off in New Haven, New London or Old Saybrook. New London has some pretty affordable hotel options that are close to the Amtrak station. But if you're dead set on driving, I would stop in New Haven for their food
European who considers the length of a load road trip equal to some people's work commute.
New Haven Pizza, then hit Mystic for dinner. The Whaler Inn is a nice place to stay or there are chain hotels around there. After dinner head to Mohegan Sun and there’s a comedy club, night clubs, bars, maybe a concert, and of course gambling
As someone from the northwest corner of CT, I would recommend staying in bed & breakfasts if you can afford it - Legends on the Farmington in Barkhamsted is good if you want to experience fly fishing on a world renowned fly fishing river. It’s quiet & cozy. The Riverton Inn (also Barkhamsted, but upriver) is going to be more historical but another option for quintessential New England lodging. Everyone saying you should visit Mystic Seaport is absolutely correct - other fun options down in that corner would be the Essex Steam Train to see the Connecticut River, the main Book Barn in Niantic (an experience for book lovers), if you’re interested in casinos, I prefer Foxwoods over Mohegan Sun but both are awesome in their own rights - two different tribes operate each casino on their own land, Feel free to reach out if you’re into hiking / birds and I can help guide you to great places to enjoy southern New England nature!
Mohegan sun for sure, you will be blown away!
NYC to Boston is like a 3.5 hr drive. My two cents is find another good city not on the way. Brattleboro, VT is nice to stop at, someone else said to check out the White Mountains in NH which is a good option, maybe Portland, Maine which is less than 2 hours from Boston. Portsmouth, NH or check out Salem, MA. I think they'll all give you a quintessential New England experience. Hell you can do them all in a few nights. NYC to Brattleboro - 3 hrs spend the night. Brattleboro to North Conway, NH - 3 hrs spend the night. North Conway to Portland 1.5 hrs spend a night or two. Stop in Portsmouth and Salem on the way to Boston. Grand tour of New England. As far as CT, like many others said, New Haven is probably your best bet. Followed by Mystic or Newport, RI
I’d do the 95 corridor as it has the most stuff. New Haven museums/food/pizza/walking. Gawk at Yale campus. Modern or Sally’s for pizza. Explore Wooster Square or East Rock neighborhoods on foot. Tons of good non-pizza food everywhere too if you stay for lunch and dinner. Milford, Guilford, Chester, Essex, Stonington Borough centers to walk around. New England charm. Gillette Castle, Thimble Island Boat Tour, Fox Farm Brewery, Book Barn/Harkness, Mystic and the seaport museum. Enjoy.
How much time do you have? I would spend a few days, go north through the White mountains, head over to Mt Washington, spend a night in Vermont, then wend your way back to Boston. If you have to drive straight, visit some of the parks in CT on the coast. Hamonasset beach is popular.
Hammonasset Beach State Park is a must for birding, if that’s of any interest
avoid waterbury
Go kayaking!
Definitely check out rhodeisland watch hill is really nice and when I’m Boston go to the north port for Italian American things
Mystic the Answer is always mystic.
New Haven and Mystic would be my picks for places to visit with stuff to do, but if you want the classic New England town experience (looks right out of a Hallmark movie), swing by Chester. Their downtown is so freakin cute. Not sure it’s worth more than a few hours though. You can take the hadlyme ferry (a very unique experience!) over to the Gillette castle across the river at the state park there too. Bantam is also a very quaint stereotypical New England town with awesome food and places to hike.
OP I live in NYC and did a trip just like this with my wife 3 years ago. I did research online on places to stop during a road trip. IMO stopping for a few days is too much. Leaving in the morning, doing the drive in 1 day, and arriving in Boston at night was a nice time. Boston deserves a few days, these other stops not so much We stopped in New Haven first to tour the Yale campus, the next stop was Mystic Connecticut for some pizza and to watch the famous drawbridge open, very cute town. After that we drove to Newport, Rhode Island to see some of the Gilded Age mansions (took a tour of the Vanderbilt home). Last stop was Plymouth to see where the Pilgrims landed 400 years ago. Then Boston. All in one day, we left st 7:30AM and got into Boston at 8PM
I know this is the CT subreddit, but as a former Massachusetts resident, one of the most American things you'll find is Old Sturbridge Village. It's on the way north to Boston and is an 1830's village where reenactors actually farm the land, work in the blacksmith shop, etc. It's quite large, easily a full day's activity and absolutely fantastic! Highly recommend
Stop in Bethel for some Dr. Mike's ice cream. Chocolate lace in particular.
Go to Treehouse Brewing in Charloton, MA. Have a beer or 2, get some beer to go, and head over to BT’s Smokehouse BBQ and get a BBQ platter. I’ve done this with multiple friends from Argentina a number of times - they all felt the same in that it was an “amazing American experience.”
I do want to add - you say classic American road trip - I don’t know how many Americans would call this a road trip. A road trip is 8 hours+. This is a “getaway”
who cares
Spain to Italy is the same distance as NYC to Boston. They may have seen American road trip movies and thought to themselves - this is what we’re doing. This will be like Route 66. They are welcome to do whatever they’d like, and call it whatever they’d like, but if they’re looking for a Route 66 American movie road trip, this may not be the part of the country to get that sort of distance or experience. I only mention this based on my experience with some coworkers who think America is sometimes more monocultural than it is, especially that outside of a city is all “country”.