Explore More: Area Adventures

Adventures List:

No matter the kind of adventure you enjoy - exploring, dining, shopping, eating, relaxing - there is something for you just outside the doors of Trailhead Inn. Here are just a few of the upcoming things going on in the area. Be sure to check back as we will update often!

June 24 - 25

Winter Park Blues From the Top

Hideaway Park in downtown Winter Park

Blues from the Top 15 - presented by the Grand County Blues Society See Event Details

July 9

Women, Wheels & Wine

Devil's Thumb Ranch Resort & Spa

Women's Mountain Bike Clinic
Whether you're an avid cyclist or your bike only gets used a couple of times a year, you'll learn something & have a great time on the Devil's Thumb Ranch trails.
The day includes lunch, wine, yoga, mini-hand treatments, use of the DTR pool, and hanging out in the hot tub, sauna & steam room at Ranch Creek Spa.
$110
Reservations: 970-726-8231 or active.com See Event Details

July 15 - 16

Winter Park Jazz Fest

Hideaway Park in downtown Winter Park

The 35th Annual Winter Park Jazz Festival will featuring: R&R with Rick Braun & Richard Elliot, Nick Colionne, Jessy J, Pg. 6ix, Marsha Ambrosius & Eric Benét, Brian Culbertson, Pieces of a Dream, Dotsero, & Selina Albright. See Event Details

July 20

Volario's Community Dinner

Volario's at Vasquez Creek Inn in downtown Winter Park

Giving back never tasted so good...
This summer Volario's is hosting Family Style Community Table Dinners every third Thursday of the month benefitting Mountain Family Center.
A four course dinner with wine pairings will be served on Volario's patio next to idyllic Vasquez Creek* featuring unique Italian inspired culinary themes each month.
Join us as we kick off the first in this unique community dinner series.
6pm - 10pm
$55/person**
A portion of the proceeds benefit Mountain Family Center.
Canned goods donations requested at the door.
(*Weather permitting. **Gratuity not included.) See Event Details

August 17

Volario's Community Dinner

Volario's at Vasquez Creek Inn in downtown Winter Park

Giving back never tasted so good...
This summer Volario's is hosting Family Style Community Table Dinners every third Thursday of the month benefitting Mountain Family Center.
A four course dinner with wine pairings will be served on Volario's patio next to idyllic Vasquez Creek* featuring unique Italian inspired culinary themes each month.
Join us as we kick off the first in this unique community dinner series.
6pm - 10pm
$55/person**
A portion of the proceeds benefit Mountain Family Center.
Canned goods donations requested at the door.
(*Weather permitting. **Gratuity not included.) See Event Details

August 19

Winter Park Uncorked Wine Festival

Hideaway Park in downtown Winter Park

Wine tasting, food samples, live music, champagne cork-off and more! See Event Details