Skip to content
Trailstead Stays
Book direct on our Guesty booking portal. Book direct: 5% off, applied automatically on our official booking site

Experience

Reunions, graduations and celebrations

Weddings, graduations, family visits and the reunions that only happen once a decade.

Is reunions, graduations and celebrations the right trip for your group?

This is for reunions, graduations, birthdays and the gatherings that only happen once a decade. The Scottsdale Social and The Sunkiss take the largest groups; The Evergreen and The Tamarack keep a Montana group under one roof. Shoulder seasons are easiest to book for a fixed date. One practical constraint: these are residential homes under house rules, not event venues. The Evergreen has six bedrooms and sleeps up to 10. Compare all four homes before you send invitations.

Compare all four homes side by side

Last reviewed 2026-09-20

Milestone trips are about the house being the venue for the group's own time rather than a base for going out. That makes gathering space, bathrooms and the published guest limit the three things worth settling before invitations go out.

These are guest homes in residential neighbourhoods, not event venues. The Evergreen sleeps up to 10 and The Tamarack sleeps up to 10, as listed on each home's booking page. Confirm gathering rules before you plan anything around a headcount.

If you are comparing both Scottsdale homes, check each home's dates and house rules separately. Each home requires its own reservation, and neither reservation establishes gathering or visitor permission at the other home.

Settle three things before invitations go out

Milestone trips go wrong on the same three points:

  • The guest limit: each home's maximum overnight occupancy, not its bed count.
  • Visitors: who can come by during the stay, which is set by each home's house rules.
  • Gathering space: where the group will actually spend the main evening.

Choosing the house for the occasion

For a Scottsdale celebration, The Scottsdale Social sleeps up to 18 and is built around shared space, with a pool, hot tub, putting green, lawn games and more than fifteen indoor games. The Sunkiss sleeps up to 16 and adds an on-site sport court. In Montana, The Evergreen's speakeasy and game room, and The Tamarack's stone fire pit and game room, give a reunion somewhere to gather after dark.

These are guest homes in residential neighbourhoods, not event venues. Read each home's house rules on visitors and gatherings before planning anything around a headcount.

A celebration weekend shape

One focal moment and plenty of downtime works better than a packed schedule:

  • Arrival day: settle in, simple dinner at home.
  • Main day: an outing in the morning, then the celebration meal at the house or a booked restaurant.
  • Last morning: a slow breakfast and photos before checkout.

Planning the logistics

Book the house first, then send dates to the group with the guest limit and the house rules attached, so nobody plans a plus-one that the home cannot take. Assign rooms before arrival, plan the main meal so the kitchen is not the bottleneck, and nominate one person as the contact with the host team during the stay. Share the booking page link with the group so everyone reads the same check-in details, guest limit and house rules.

For a larger family or friend group in one destination, two homes booked as separate stays can each host part of the group, with the celebration meal at a restaurant booked well ahead rather than at either house.

Related planning

Questions groups ask

Can we hold a wedding or event at a Trailstead home?

No. These are residential guest homes, not event venues. Check each home's house rules for visitor and gathering limits.

What if our group is bigger than one home?

In the same destination, the two homes can be booked as two separate stays, each with its own reservation, guest limit and house rules.

Which home sleeps the most guests?

The Scottsdale Social, which sleeps up to 18.

Stays

Homes that suit this trip

Scottsdale, Arizona

The Scottsdale Social

Made to play. Built to gather.

5 bedrooms · 9 beds · 3 baths · 4.92 (71) · checked 23 Sep 2026

The larger of the two Scottsdale houses, built around shared time. Five bedrooms and nine beds, a private backyard with pool, hot tub and putting green, and more than fifteen games for the evenings nobody wants to go out.

  • Group celebrations and reunions
  • Golf trips
  • Holiday gatherings

Sleeps up to 18. Five bedrooms, nine beds and three bathrooms. Maximum 18 guests overnight.

Scottsdale, Arizona

The Sunkiss Scottsdale

Serve. Swim. Stay awhile.

5 bedrooms · 8 beds · 3 baths · 4.93 (60) · checked 23 Sep 2026

A Scottsdale home shaped around outdoor time. Four king bedrooms and a bunk room, a private pool and hot tub, and a sport court set up for pickleball and basketball. It suits groups who want to play during the day and stay in for a long evening together.

  • Golf and pickleball groups
  • Family and multigenerational trips
  • Cooler-season desert escapes

Sleeps up to 16. Five bedrooms, eight beds and three bathrooms. Maximum 16 guests overnight.

Somers, Montana

The Evergreen at Flathead Lake

Room to reconnect. Montana to explore.

6 bedrooms · 10 beds · 3.5 baths · 4.98 (42) · checked 23 Sep 2026

A six-bedroom Montana home for groups that want one roof instead of several. A private hot tub and barrel sauna outside, a speakeasy and game room inside, near Flathead Lake and Glacier Country.

  • Multigenerational family trips
  • Flathead Lake and Glacier planning
  • Fall and winter gatherings

Sleeps up to 10. Six bedrooms, ten beds and 3.5 bathrooms. Maximum 10 guests overnight per local regulations.

Lakeside, Montana

The Tamarack

Adventure out. Exhale in.

6 bedrooms · 9 beds plus trundle · 4.5 baths · 5.0 (12) · checked 23 Sep 2026

A six-bedroom Montana lodge for groups that plan to be outside most of the day. Hot tub, sauna, fire pit and game room, room for gear and vehicles, and a setting built for golden-larch fall drives and winter ski days.

  • Lake trips
  • Group retreats
  • Ski and winter weekends

Sleeps up to 10. Six bedrooms, nine beds plus trundle and 4.5 bathrooms. Maximum 10 guests overnight.