Stevenson Station, Monroe, Connecticut, circa 1910

Stevenson Station, Monroe, CT — postcard, circa 1907-1915

Itinerary for 2026 Trip to Connecticut

August 7 - 17, 2026

Hi everyone!
We're planning our Connecticut trip for August 7 - 17, 2026 and wanted to share our current thinking:

  • Allison and Hudson: We want to make sure the plan works well for you two.
    • NYC may end up being the easiest place to meet up, especially around your two days off (the Aug 8/9 matinee and the Aug 10 museums day) — if so, a hotel outside the city for those nights might make more sense than driving back to Monroe each night (see Aug 8-10 below)
    • The NYC days are still a brainstorm, with the Broadway show being the strongest plan so far
    • We don't need to spend the whole time in NYC — could be a day or two in CT or potentially NJ.
    • Additional thought: instead of Grandma and Grandpa driving all the way to JFK to pick us up, we could stay with you in NJ Friday night on arrival, then head into the city together Saturday
  • Early stages: This plan is still taking shape, so all feedback and suggestions are welcome!

Calendar Overview

Fri, Aug 7
Arrival Day - Flight from Seattle ✈️
Confirmed CT
Sat, Aug 8
"Lost Boys" Matinee (option A)
Tentative NYC
Sun, Aug 9
"Lost Boys" Matinee (option B)
Tentative NYC
Mon, Aug 10
NYC Museums - Met + Natural History
Tentative NYC
Tue, Aug 11
New Haven day near Yale; evening Perseids observing
Tentative CT
Wed, Aug 12
Sailing with Grandpa Gary ⛵
Tentative CT
Thu, Aug 13
Mystic Seaport Day Trip
Tentative CT
Fri, Aug 14
Cory's (Long Beach) or Gillette Castle/Webb Mountain Park
Tentative TBD
Sat, Aug 15
Cory's (Long Beach) continued, or open day in CT — Eric's family also back from Montana today
Tentative TBD
Sun, Aug 16
Possible Visit to Eric's 👨‍👩‍👧‍👦
Option CT
Mon, Aug 17
Departure Day - Flight Home ✈️
Confirmed CT
Fri, Aug 7 - Arrival Day
✈️ Outbound Flight - Alaska 34 Confirmed
9:29 AM
Seattle (SEA) → New York JFK
Departure: 9:29 AM | Arrival: 5:55 PM
Drive to Monroe, CT Confirmed
Grandma and Grandpa's house
Sat, Aug 8
"Lost Boys" Matinee - NYC Day (option A) Tentative
Lost Boys — 2:00 PM
With Cory's family, Grandma and Grandpa, Brian's family, and Allison's family — spend the day in NYC, dinner in the city
Note: Only happens on Aug 8 OR Aug 9, not both
Backup show: Titanique (also 3:00 PM this day) — a second choice if Lost Boys doesn't work out; open to other show suggestions too
Lodging: Considering a hotel in Stamford or Norwalk, CT (or White Plains/New Rochelle, NY) for Saturday and Sunday nights (Aug 8-9) instead of driving back to Monroe, CT — cheaper than Manhattan, on Metro-North so we can train into the city instead of driving/parking there, and cuts down on back-and-forth driving during this NYC-heavy stretch (matinee + Monday's museums day)
Sun, Aug 9
"Lost Boys" Matinee - NYC Day (option B) Tentative
Lost Boys — 3:00 PM
With Cory's family, Grandma and Grandpa, Brian's family, and Allison's family — spend the day in NYC, dinner in the city
Note: Only happens on Aug 8 OR Aug 9, not both
Lodging: Second night at the NYC-area hotel, if booked (see Sat, Aug 8)
Mon, Aug 10
NYC Museums Day Tentative
NYC
Allison is taking the day off work
• Metropolitan Museum of Art
• American Museum of Natural History, including the Hayden Planetarium
• If staying at the NYC-area hotel, check out after museums and drive back to Monroe, CT
Tue, Aug 11
New Haven Day Near Yale Tentative
New Haven, CT
Allison is taking the day off work
Exploring near Yale — e.g. Yale University Art Gallery, Peabody Museum of Natural History, downtown New Haven for pizza
🔭 Perseids Meteor Shower Observing Tentative
Evening
Yale's Leitner Observatory, New Haven, CT
Public Night telescope observing — leitnerobservatory.yale.edu/public-nights/telescope-observing
Perseids shower expected to peak this night
Wed, Aug 12
Sailing in CT Tentative
CT
Grandpa Gary races every Wednesday, so we'll likely go sailing with him
Thu, Aug 13
Mystic Seaport Day Trip Tentative
Mystic Seaport, CT
Fri, Aug 14
Option A: Visit Cory's Family in Long Beach, NY Tentative
Long Beach, NY
Overnight — continues into Sat Aug 15
Option B: Gillette Castle or Webb Mountain Park Tentative
CT
One or the other — not yet decided
Only one of these two options happens — see TODOs below
Sat, Aug 15
Option A: Continue Visit at Cory's Tentative
Long Beach, NY
Finish visit with Cory's family and return to CT
Option B: Open Day in CT Tentative
Eric's family returns to CT from Montana today
Sun, Aug 16
Possible Visit to Eric's Option
Eric's house
Now that his family is back in CT (as of Aug 15)
Mon, Aug 17 - Departure Day
Leave for JFK Airport Confirmed
9:00 AM ET
Grandma and Grandpa's (Monroe, CT) → JFK Airport
~2 hour drive, plus ~2 hours early for 1:00 PM flight
✈️ Return Flight to Seattle - Alaska 23 Confirmed
1:00 PM
New York JFK → Seattle (SEA)
Arrival: 4:19 PM
Other Activities / Brainstorm
Ice Cream Shop Visit Brainstorm
Visit the Ferris Acres Creamery ice cream shop in CT — ferrisacrescreamery.com
Planning TODOs

Items that need confirmation, planning, or coordination: