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Now that we live in Boston, we are lucky to have some of the most beautiful vacation destinations on our doorstep.
We’ve only been here a short while, but I’ve been fortunate enough to take a couple of weekend trips since moving here!
If you’re after a long weekend destination, here are our favorite ones so far:
1. Boston, Massachusetts
Biased; I know since we live here!
But Boston is a great place to visit over a long weekend!
Think brick houses, ivy, and streets littered with amber-colored leaves.
The city is public transport friendly, so you don’t need a car to enjoy your time here and it is easy to navigate on foot.
Looking for an afternoon walking tour? Check out my guide to spending an afternoon in Boston!
2. Philadelphia, Pennsylvania
Usually ignored for bigger, flashy neighbors such as New York and Boston, Philly’s day has come!
This historical city has so much to see and learn from, particularly when it comes to American history.
Here you’ll get to visit the Liberty Bell, find out more about the American Revolution and wander down America’s oldest residential street (Elfreth’s Alley).
Not too fond of history?
Philly has AH-MAZING drool-worthy food (Philly cheesesteaks!) and locally known art galleries to envy NYC.
3. New York City, New York
Speaking of NYC… You can never run out of places to explore or things to do in the city that never sleeps.
I’ve spent weeks exploring this city, only to keep on wanting to come back.
While I would never live here, this city has something for everyone.
4. Granby, Connecticut
Connecticut is not at the top of international visitors “must visit” destinations, but you don’t get more New English than this beautiful state.
Granby, often touted by residents as a “hidden gem” has endless local farms and woodland walks.
Perfect if you love food (their farm to table eateries are cheap and delicious) and they have the best farm-fresh ice cream on the East Coast.
Check out my best restaurants and farms guide or my best walks guide to learn more about Granby, CT!
5. Chicago, Illinois
Where do I even start?
Famed for public art (where else in the world can you see a Pablo Picasso statue in public??) and the world’s best museum (as named by Trip Advisor) Chicago is one of those cities where you can never run out of places to explore.
What did you think? What are some of your favorite weekend trips from the East Coast?
Best local eats in Chicago, IL