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Three Favorite Cities for a Long Weekend Visit

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nelsonmuntz

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Looking for places that don't quite justify a full vacation, but a weekend trip would be a lot of fun.

Rules:

Assume pandemic is over​
Can not select the obvious: New York, Boston, Los Angeles or San Francisco​
If you want to include non-North America, make it a separate list:​


My list:

1) Chicago - This is one of the coolest weekend getaway cities in the world. I love this place. The big flagship hotels downtown like the Grand Hyatt, Intercontinental or Palmer House are really cool, but there are at least 20 great local hotels in Old Town or on the Gold Coast that I would recommend over the chains. The city is a little big to walk, but the El can get you anywhere you need to go for a weekend. Recommend: Walk downtown, Cubs game then hang out in Wrigleyville afterward, dinner in Lincoln Park. Lots of cool museums if you are into that.

2) Philadelphia - The city center is elegant and fun. A lot of the places you would want to go are walkable, and if you want to slip into the burbs for a day trip, there are some nice areas and cool restaurants along the Main Line.

3) Montreal - I have only been there 3 times, all for work, and have had a blast every time. I couldn't tell you wear to go or stay, but it is a cool place to visit.

Honorable mention:

Calgary - it has been a while since I have been here, and the flight is a killer, but this is one of my favorite cities in North America. Go during the Stampede if you can.

Austin - I haven't been here in about 8 years, but I love this city. It was starting to get a little sprawly by they early 2010s, and I don't imagine that has gotten better.
 
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Second Philly...

Assume pandemic and pop-up protests/current political climate subside to level of even 5 years ago (big ask)... I would put DC on the list. Walkable/decent public transportation, ethnic restaurants galore and plenty of free museums/points of interest/activities.
 

storrsroars

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For me, it's all about going "home". Although I will say I need to "experience" LA at some point. I've been there many times, but almost always in the same areas.

1. Mexico City. It's been 25 years since I've lived there, but have never been back. Well past time. Probably the best food city in N. America. The one issue is that it's a 7 hour flight with connections from Pittsburgh, so that eats into a lot of a long weekend.

2. DC. Despite visiting many times and living in Alexandra, there's still a ton I haven't seen. I need an Ethiopian dinner fix.

3. Boston. This would be primarily to catch up with friends, although there are a number of old haunts worth revisiting. Again, overdue since I haven't been back in 20 years.

Probably the only city I haven't been to that would interest me for a weekend is Charleston SC.
 

uconnbaseball

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Boca Raton, Little Rock, and Phoenix (apart from the summer) are all nice to visit. Little Rock has some of the best food I have ever had and Boca Raton is gorgeous.
 
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Second Philly...

Assume pandemic and pop-up protests/current political climate subside to level of even 5 years ago (big ask)... I would put DC on the list. Walkable/decent public transportation, ethnic restaurants galore and plenty of free museums/points of interest/activities.
I have family living about 45 minutes west of Philly, so I'll third that. My wife has become a big advocate of telling people all the things to be done on vacation in Philly, southeastern Pennsylvania (stretching out to Amish Country just to the east of Lancaster), and northern Delaware.

There was a mention of food in this thread. Best steak and barbecue that we ever had was in Kansas City when we visited for the women's basketball final four.
 
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HuskyHawk

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@nelsonmuntz Pre Covid I traveled to Austin 2-3 times a year for work. Technically once during Covid at the end of February into March. The main entertainment, music and bar area hasn’t been changed by the sprawl (but there is massive highway construction). There are a lot of new breweries that have been added to the mix in the last couple of years. BBQ remains great. So I still think it fits your list. Others have recommended San Antonio to me, but I have not gone yet.

New Orleans tops my list in this category. Perfect four day city because I can’t eat/drink at that pace much longer than that anyway.

Burlington Vermont in the summer or fall is a nice 3 day weekend town.

I agree Chicago belongs on the list, in the spring through fall. So much you can do there. My favorite big U.S. city by far.

I also think Sonoma - Napa makes a superb long weekend destination. You can stay in Marin county if you want to be closer to SF or up in Calistoga for the hot springs. Lots of nice restaurants to go with the wineries. Redwood forests nearby. The scenery is wonderful and the best time of year is probably around late October to November.
 
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Not sure why Chicago isn't on the "obvious" list.

Have to agree with Austin, DC and Philly.

Can't believe someone listed Little Rock. Besides one really great steakhouse (actually in North Little Rock), I find the food there to be average and the city to be dumpy. Spent tons of time there from 2006-2013.

For major cities, I have to put Atlanta on the list. Good food and culture scene.

If we are venturing outside of major cities, St. Augustine, FL. It used to be a tourist trap, particularly in the old town, but it's really improved in the last 10-15 years. Just enough to cover a 3-4 day trip in terms of stuff to see, outstanding restaurant scene, and a great beach.
 
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I’ve only driven for long weekends, so considering that condition places I’d love to go for a long weekend near Norwalk:

1) Hudson Valley: anywhere between Beacon and Hudson: food, nature, art. Lots of boutique stuff if you’re into that, but Fishkill and Poughkeepsie are good options rich with affordable chain lodging.

2) Western Mass and Berkshires. Same reasons for Hudson Valley but you can buy weed.

3) Rust Belt Eastern PA. Bethlehem, Easton and Jim Thorpe are all favorites of mine. Jim Thorpe is one of the favorite small towns I’ve visited...so unique.
 
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storrsroars

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3) Rust Belt Eastern PA. Bethlehem, Easton and Jim Thorpe are all favorites of mine.
When in Easton, check out Two Rivers Brewing. Old coffee colleague of mine (Troy) is one of the co-owners. Solid beer, great burgers.
 
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I quite enjoy San Antonio. A number of sightseeing opportunities around the city, and then food, drink, and some entertainment along the Riverwalk area. An excellent site in the past for the women's basketball final four.
 

8893

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I quite enjoy San Antonio. A number of sightseeing opportunities around the city, and then food, drink, and some entertainment along the Riverwalk area. An excellent site in the past for the women's basketball final four.
And for men’s in 2004...
 
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Looking for places that don't quite justify a full vacation, but a weekend trip would be a lot of fun.

Rules:

Assume pandemic is over​
Can not select the obvious: New York, Boston, Los Angeles or San Francisco​
If you want to include non-North America, make it a separate list:​


My list:

1) Chicago - This is one of the coolest weekend getaway cities in the world. I love this place. The big flagship hotels downtown like the Grand Hyatt, Intercontinental or Palmer House are really cool, but there are at least 20 great local hotels in Old Town or on the Gold Coast that I would recommend over the chains. The city is a little big to walk, but the El can get you anywhere you need to go for a weekend. Recommend: Walk downtown, Cubs game then hang out in Wrigleyville afterward, dinner in Lincoln Park. Lots of cool museums if you are into that.

2) Philadelphia - The city center is elegant and fun. A lot of the places you would want to go are walkable, and if you want to slip into the burbs for a day trip, there are some nice areas and cool restaurants along the Main Line.

3) Montreal - I have only been there 3 times, all for work, and have had a blast every time. I couldn't tell you wear to go or stay, but it is a cool place to visit.

Honorable mention:

Calgary - it has been a while since I have been here, and the flight is a killer, but this is one of my favorite cities in North America. Go during the Stampede if you can.

Austin - I haven't been here in about 8 years, but I love this city. It was starting to get a little sprawly by they early 2010s, and I don't imagine that has gotten better.
A lot of talk about The Palmer House closing for good which would be devastating to the city. I absolutely love the place and have had some incredible times there, it's my favorite lobby in the country.
 
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For me, it's all about going "home". Although I will say I need to "experience" LA at some point. I've been there many times, but almost always in the same areas.

1. Mexico City. It's been 25 years since I've lived there, but have never been back. Well past time. Probably the best food city in N. America. The one issue is that it's a 7 hour flight with connections from Pittsburgh, so that eats into a lot of a long weekend.

2. DC. Despite visiting many times and living in Alexandra, there's still a ton I haven't seen. I need an Ethiopian dinner fix.

3. Boston. This would be primarily to catch up with friends, although there are a number of old haunts worth revisiting. Again, overdue since I haven't been back in 20 years.

Probably the only city I haven't been to that would interest me for a weekend is Charleston SC.
Mexico City is awesome and is now a yearly visit for me pre-Covid. I expect to go back in the Spring. Awesome food everywhere, amazing architecture and museums and just a super vibrant metropolis with nice people. I'm surprised I don't run into more Americans/International travelers down there considering it has everything you could ever want in a city and it's so cheap.
 

storrsroars

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A lot of talk about The Palmer House closing for good which would be devastating to the city. I absolutely love the place and have had some incredible times there, it's my favorite lobby in the country.
Me and three colleagues were banned from there. Major food fight in a suite. It was a nice hotel though.
 
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Mexico City is awesome and is now a yearly visit for me pre-Covid. I expect to go back in the Spring. Awesome food everywhere, amazing architecture and museums and just a super vibrant metropolis with nice people. I'm surprised I don't run into more Americans/International travelers down there considering it has everything you could ever want in a city and it's so cheap.
Can't do it. Still recovering from whatever bug/parasite I caught there in 2015.
 

storrsroars

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Haha, you don't hear that every day.
National Hardware Show, 1993. The operations team had already been in town for a week, and they get fruit baskets on arrival. Seven days later that stuff was pretty ripe...
 

Fishy

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Long weekend means driving and driving means leaving from the northeast because this is a UConn board.

1) Burlington, Vermont.
2) Bar Harbor, Maine.
3) Portsmouth, NH.

If you’re including places like Calgary or Mexico City which are not really long weekend spots for northeasterners unless they’re masochists who like long flights....

1) Vancouver.
2) Key West.
3) The moon.
 
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1) NOLA: 4 days is all I can handle at this point

2) Tampa- Because i love Tampa

3) Montreal- Always fun. Cool people, and I came back with a great story every time.

Chicago, ATL, NYC, Vegas would all be in the "obvious" category.
 

storrsroars

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Long weekend means driving and driving means leaving from the northeast because this is a UConn board.

1) Burlington, Vermont.
2) Bar Harbor, Maine.
3) Portsmouth, NH.

If you’re including places like Calgary or Mexico City which are not really long weekend spots for northeasterners unless they’re masochists who like long flights....

1) Vancouver.
2) Key West.
3) The moon.
It is a UConn board, but it's quite obvious that many here no longer live in CT.

One doesn't really do long weekend drives from Pittsburgh as a four-hour drive gets you nothing better than Cleveland, Detroit or Buffalo. DC and Toronto are about 4.5 hours.

If memory serves me right, isn't Bar Harbor about a seven hour drive from Stamford?
 

8893

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Thoughts on Newport, RI for a weekend in late September for wedding anniversary, with wife, 14-year old daughter and one of her friends?

I've been there maybe twice for a total of 24 hours or less.

We also considering Newburyport, MA and Portsmouth, NH.
 
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storrsroars

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Thoughts on Newport, RI for a weekend in late September for wedding anniversary, with wife, 14-year old daughter and one of her friends?

I've been there maybe twice for a total of 24 hours or less.

We also considering Newburyport, MA and Portsmouth, NH.
I wonder what today's kids think of the ridiculousness of the mansions and the often un-PC ways the money to buy those manses was earned.

Been to Newburyport a few times in the 80s as an ex-wife's aunt lived there. Never gave it a thought as a weekend destination. I'd think Portsmouth would be more interesting for teens, but I don't have teens so what do I know.
 

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