May 28 — May 31, 2026 · Late May

Woodstock

NYC → Hudson Valley · Thu eve option · Ilan & Kayla · Naomi & John

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Getting there · Road trip from NYC · ~2–2.5 hrs

New York City Thu eve (if Jon can work remote Fri) or Fri AM TBD May 28 – 29
Drive
I-87 N · NY Thruway
Woodstock, NY Ulster County Arrive Thu late or Fri
4 travelers · 2 couples Thu night = head start before Friday rush Split gas & tolls
Woodstock, NY Checkout Late AM Sun May 31
Drive
South on I-87
New York City Drop-off TBD Afternoon Sun May 31
Last day upstate Sunday traffic: plan buffer

Packing List

Things to Book Ahead of Time

Research & Considering

Where to Stay

These cards are options you’re comparing — nothing here is booked until someone confirms and pays. Listing photos appear when you paste an Airbnb link (real listing images) — we don’t use stock photos for stays. Sort into walkable vs a short drive, or leave in Still deciding until the group picks.

In or beside the village

Walkable to Tinker St. · minimal driving after you park

  • Stroll to coffee, dinner, and shops without a DD rotation
  • Great if you want late evenings in town and easy mornings
  • Often smaller or pricier per bedroom for peak summer weekends

A few minutes out

Short drive into town · often whole-house rentals

  • More space, yards, and parking for two cars — often better for four adults
  • Quieter nights; plan on driving for dinner or carpooling
  • Watch winter/spring mud season on mountain roads (June is usually fine)

Where to Eat

Budget Tracker

Gas & tolls
~$80–120
Lodging
split 4 ways
Stays
TBD
Food & outings
TBD
Ballpark (per person)
$200–400+
Airbnb / house rental (3 nights, ÷4) TBD
Gas & tolls (I-87, split) ~$20–35 pp
Dinners in town ~$40–80 pp
Hikes / swimming / misc ~$0–40
Groceries & breakfast in ~$30–60 pp

Cost ballparks · Hudson Valley weekend (USD)

Everything is in US dollars. Tweak numbers as you lock in the house and restaurants.

Splitting 4 ways: assign one person to book lodging and settle up with Venmo after.

Weather Forecast · May 28 – May 31

Fetching forecast data...

Trip Assistant · Ask About Woodstock & the Catskills