Three places this could work

Why it works

Good access for the 26 East Coast attendees, retreat-style properties that hold 42 without feeling like a conference hotel, strong food and wine experiences, and an atmosphere that supports leadership strategy without feeling corporate.

Tradeoffs

• — Austin and San Francisco attendees connect through Charlotte or DC, adding 2–3 hours each way.
• — Limited venue inventory at your size — realistically two properties, both of which need booking now.
• — Mid-October is peak leaf season, so rates run 15–20% above shoulder.

Why it works

Direct flights from all five departure cities, the shortest average door-to-door time of anywhere considered, and enough hotel inventory that you can negotiate rather than accept.

Tradeoffs

• — Mid-October averages 84°F, which limits outdoor activity to mornings and evenings.
• — Downtown venues feel like business travel, which works against the reconnection goal.
• — F&B runs roughly 12% higher than Virginia.

Why it works

The strongest sense of actually leaving work behind. Mountain properties with real separation, excellent food scene, and the kind of setting where the informal conversations you're hoping for actually happen.

Tradeoffs

• — Hardest airport of the three — most attendees connect, and West Coast travel becomes a full day.
• — Ground transportation costs roughly $2,800 more because of airport distance and shuttle needs.
• — Weather is the least predictable in October, which matters given you have one outdoor activity.