Quick answer
To plan a family reunion in the Catskills, start 9–14 months out: pick a non-peak weekend (May, June, September or October), book an all-inclusive venue so meals are handled, name a family point person, collect a headcount and room list, order matching shirts, and plan one group photo and one big dinner.
Why the Catskills work so well for reunions
The Northern Catskills sit within a half-day drive of New York City, New Jersey, Connecticut, Boston, Albany and Syracuse, which means most branches of a Northeast family can arrive Friday night without anyone taking a flight. Around East Durham — the "Irish Alps" — Irish-American families have been holding reunions for generations, and many resorts there are built around feeding and entertaining big groups.
The single biggest decision you'll make is all-inclusive versus do-it-yourself. When lodging, three meals a day and evening entertainment come in one per-person price, nobody spends the weekend running to the grocery store, and cousins who haven't seen each other in years actually get to sit down together.
The 12-month reunion timeline
12–14 months out: dates and venue
- Survey the family for two or three possible weekends.
- Favor non-peak weekends in May, June, September or October, or Sunday–Thursday in July and August — better availability and lower rates.
- Call the venue, hold rooms and ask about group rates and minimums (midweek group packages often need 10+ rooms).
9–12 months out: the money conversation
- Decide who pays for what: most families have each household book and pay for its own rooms, with a small "kitty" for shirts, decorations and a cake.
- Share the per-person rates and the kids' pricing early — many all-inclusive groups let young children stay free on certain nights.
- Set a deadline for each household to place its deposit.
6–9 months out: the room list
Build a shared spreadsheet with every household, number of adults and kids, preferred bed setup and arrival day. Grandparents usually want ground-floor rooms close to the dining room; families with toddlers want to be near the pool; teenagers want to be as far from their parents as possible.
3–6 months out: the fun parts
- Order matching reunion shirts — pick one bright color so the group photo pops.
- Plan one structured moment per day: a welcome toast, the group photo, a memory table with old pictures, a talent show or trivia night.
- Tell the venue about birthdays, anniversaries and dietary needs.
1 month out: final details
- Send a one-page itinerary to every household.
- Confirm the headcount and the time and place of the group photo.
- Pack name tags — the in-laws will thank you.
A sample reunion weekend
- FridayCheck in, dinner on arrival, then live music in the pub.
- SaturdayBreakfast buffet, pool and lawn games, the group photo on the lawn, lunch buffet, a BBQ or three-course dinner, and dancing into the night.
- SundayBreakfast, goodbyes on the porch — and someone volunteers to plan next year.
Keep every generation happy
Grandparents want comfortable chairs, shade and a front-row seat for the music. Parents want meals they don't have to cook and a pool where they can see the kids. Kids want a playground, a pool and other kids. Teens want Wi-Fi and freedom. A resort with a heated pool, lawn games, a pub with live music and three meals a day covers all four at once.
Book early — reunions fill fast
Popular reunion venues fill a year ahead. At Gavin's Irish Country Inn in East Durham, over 50 reunions were already booked for 2027 by October 2026, and the inn regularly hosts two or three reunions on the same weekend. If you have a date in mind, hold the rooms now and sort out the details later.
Frequently asked questions
How far in advance should you book a family reunion venue?
Nine to fourteen months ahead is ideal. Popular weekends at Catskills resorts fill a year out, so hold your rooms as soon as the family agrees on a date.
What is the cheapest time to hold a family reunion?
Midweek (Sunday–Thursday) stays and non-peak months like March, April, May, September and November usually carry the lowest group rates.
How do you split the cost of a family reunion?
Most families have each household book and pay for its own rooms, and collect a small shared fund for shirts, decorations, a cake and the group photo.
What should be included in a reunion package?
Look for lodging, three meals a day, evening entertainment and use of the pool and grounds in one per-person price, plus group perks like free upgrades or free kids on certain nights.
How many rooms do you need for group rates?
It varies by venue. At Gavin's, midweek group packages generally require 10 or more rooms; weekend group packages run March through November.
By the Gavin family · Gavin’s Irish Country Inn, East Durham, NY · Updated
