Northeast Weekend: Maximum Miles

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Anything I have chosen to add on post-trip, I will put in bold.

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Wednesday 8/16

• Leave home at 2:30pm Wednesday after work
• Drive through both DC and Delaware (been to both places so no need to stop for this road-trip)
• Arrive in Philly at 9pm and stop for cheese steaks!
• Dalessandro’s Steaks (close at 10pm on weeknights)
  • BEST PHILLY CHEESE STEAKS IN THE COUNTRY!!!
• Arrive at Liberty State Park, NJ around 12:00am
  • Offers beautiful view of NY skyline along with the statue of liberty. Closes at
• 10pm. Will have to park car outside of park and then walk in. (we just did street parking nearby for free)
• Drive into/through Times Square on the way North! (45 min from State Park)
  • Arrive around 1:30am
• Finish out the long night of driving and get to Air B & B in Greenwich, CT (just beyond an hour away, so arrive around 2:30am)
  • https://www.airbnb.com/rooms/1407533429219362515?check_in=2026-03-11&check_out=2026-03-12&guests=1&adults=4&s=67&unique_share_id=7df709f3-78b0-4f67-a10a-e69492a0b72e ($269)

Thursday 8/17

• Leave NJ and begin drive further North at 7:30am
• Arrive in New Haven Connecticut around 10:30am
  • Silver Sands State Park
    • Jump in the ocean for a morning swim!
    • Go here first as it is on the way to New Haven
  • Yale University
    • Walk around and explore the campus
    • I remember being underwhelmed… Used to grow up hearing how prestigious Yale was and assumed the facilities would be state of the art…
  • East Rock Park
    • We ended up driving by it and looking at the view but not actually hiking anything
  • Poppy’s Coffee + Kitchen
    • Super good food and coffee!
  • Not a ton to do here in New Haven
• Leave New Haven at 1pm for Hartford, arrive at 1:45pm
  • State Capitol
  • Bushnell Park
    • America’s first publicly funded park (est. 1854)
    • Beautiful open green space in the heart of downtown Hartford
    • Peaceful walking paths and tree-lined lawns
    • Lots of monuments throughout!
    • Statue of Israel Putnam
      • Historic Revolutionary War monument located in Bushnell Park
  • Soldiers and Sailors Memorial Arch
    • Look at the view of Hartford from the top of it and walk through the tunnels/stairs inside of it!
  • 1914 carousel
    • Built in 1914, over 100 years old
    • One of the oldest surviving Stein & Goldstein carousels in the U.S.
  • Hartford was one of the first real cities we got to explore on our Northeastern road trip, so we were very excited! It was an extremely clean city with a lot of cool monuments and murals. Never felt unsafe the whole time! The only downside I would say was a lack of people, it felt like we were kind of the only people in the city.
• Leave Hartford at 3:15pm and arrive in Newport, RI at 5