Well, tomorrow I take my first Southwest flight since they overhauled their entire business model. Feels weird not setting ten reminders to check in exactly 23 hours and 59 minutes before takeoff. I’m a little worried I’m going to miss the drama of trying to save two seats for my friends who forgot to check in and are in Group C. Guarantee I land a middle seat and there’s no space for my bag…
For those of you who've already flown the new Southwest:
Will report back next week.
Three Days in Early May Worth Knowing About
Friday, May 1 — A Letter From the Assessor
Douglas County's Assessor's Office releases the 2026 Real Property Notices of Value tomorrow, and the appeal window opens the same day. The catch: only property owners whose value, use, or ownership changed since the last cycle will get a notice — that's less than 10% of all DougCo property owners. If you're in that 10%, though, this is your one shot per cycle to push back before the new number sticks. Written objections (by mail or online) are due June 8.
The Assessor's Office at 301 Wilcox Street in Castle Rock is open 8am–5pm Monday through Friday, and they encourage in-person meetings if you have questions about your assessment (which you can schedule online).
Saturday, May 2 — A Garage Sale Hunter's Dream Day in Highlands Ranch
HRCA's annual Community Garage Sale runs all day Saturday, with 100+ participating households scattered across the neighborhood. If you're a garage sale lover from anywhere in DougCo, this is the day to plot a route — the digital map of every participating household is already live, so the whole point is browsing the wider community, not just walking your block.
If you're thinking about hosting a sale yourself, two heads-ups: seller applications close TODAY (Thursday, April 30), and you'll need to swing by one of HRCA's four rec centers to purchase an HRCA-approved sign before Saturday.
Sunday, May 3 — A Free 25th Anniversary Concert
The Highlands Ranch Concert Band, 80 musicians strong, ranging in age from teens to folks in their 80s and made up entirely of volunteers, is celebrating 25 years with a free anniversary show at Rock Canyon High School at 3pm. The "Encore!" program walks through the band's most-loved repertoire over the years: Arabesque, Gershwin by George, Symphonic Beatles, and selections from West Side Story.
The afternoon also doubles as a reunion of the four conductors who've led the band since its founding in 2001 — including founding conductor Mark Wurst and former associate conductor Niel Guy, who's performing a trombone solo. Reception after the show.
The band's mission has always been to keep their concerts free, funded by local sponsors, donations, and the Scientific and Cultural Facilities District. If you've never caught one of their shows, this is the one.
Comfort Keepers
Hiring Caregivers in Douglas County
You don't need a medical degree. We will train you, if more skills are needed! You already have life experience, a good heart, and the willingness to show up for someone who needs it...come share those with a senior.
Comfort Keepers is looking for caregivers right here in Douglas — people who want flexible hours and work that actually means something.
Dollar-for-dollar donation matching, gym stipend, matching 401k, Medical Insurance...real benefits for real people.
It's simple to apply online and we'll schedule an interview within 72 hours.
Apply today → Our Next Great Caregiver's Application
Help Wanted
Local jobs and opportunities across Douglas County.
If you’re hiring, reach out at [email protected] for a free posting.
We just had our 7th Dinner Club and have officially surpassed 250 individuals attending, with many attending multiple times. We’ll be in Lone Tree on Wednesday, May 13th. Would love to have you try it out!
We also had a very successful Couples Dinner (55+) last night. If you’re interested in being on the interest list for future Couples Dinners (any age), please respond to the poll below and provide your age(s):
Saddle Up
Music & Concerts
Tailgate Tavern & Grill - The Country Music Project (Inside Stage) - Thu 4/30, 7:30pm–11:30pm
Cherokee Ranch & Castle - Freddy Rodriguez Legacy Jazz Band - Fri 5/1 - $79.45 - tickets
Honnibrook Craft Meadery - Josh Blackburn: Live In Castle Rock - Fri 5/1, 6:00pm–9:00pm
Stagecoach Saloon - THE BAND THESE GUYS! - Fri 5/1, 6:30pm–10:30pm
Wide Open Saloon - Sideways 7 - Fri 5/1, 7:00pm–10:30pm
Lone Tree Arts Center - Lone Tree Symphony Orchestra Presents: American Spirit - Fri 5/1, 7:30pm
Takoda Tavern - Grizzly Gophers - Fri 5/1, 7:30pm–11:30pm
Sinners & Saints - Tyler Stanfield - Live at the Altar - Fri 5/1, 8:00pm–9:30pm
Tailgate Tavern & Grill - Mile Hi Groove (Inside Stage) - Fri 5/1, 8:30pm–12:30am
Wide Open Saloon - Saturday Acoustic Set - Sat 5/2, 2:00pm–5:00pm
Sinners & Saints - Carson McHaney - Live at the Altar (Dirty Derby Special) - Sat 5/2, 3:00pm–5:00pm
Tailgate Tavern & Grill - Mid Life Crisis (Patio) - Sat 5/2, 6:00pm–10:00pm
105 West Brewing Company - Live Music: Sarah P and the Dirty Logger - Sat 5/2, 6:30pm–9:30pm
Stagecoach Saloon - The Walker Williams Band - Sat 5/2, 6:30pm–10:30pm
Wide Open Saloon - 9's A Pair (The Fireman Band) - Sat 5/2, 7:00pm–10:30pm
Lone Tree Arts Center - 100 Years of Blues with Elvin Bishop and Charlie Musselwhite - Sat 5/2, 7:30pm - $50-65 - tickets
Takoda Tavern - Hard 45 - Sat 5/2, 7:30pm–11:30pm
The Studio @ Mainstreet - Stone Cold Band - Sat 5/2, 8:00pm–11:00pm
Tailgate Tavern & Grill - Mile Hi Groove (Inside Stage) - Sat 5/2, 8:30pm–12:30am
The Studio @ Mainstreet - WAGS and the BOYS - Sun 5/3, 12:00pm–4:00pm
Tailgate Tavern & Grill - Sarah P and the Haypullers (Patio) - Sun 5/3, 12:00pm–4:00pm
105 West Brewing Company - Live Music: Giant Zero - Sun 5/3, 2:30pm–5:30pm
Rock Canyon High School - Encore! 25 Years of Music & Memories - Sun 5/3, 3:00pm–5:00pm
PACE Center - Tarab, Beyond Time: An Evening with the National Arab Orchestra - Tue 5/5, 7:30pm - $69-199 - tickets
Food & Drink
Cherokee Ranch & Castle - Afternoon Tea at the Castle - Fri 5/1 - $75 - tickets
105 West Brewing Company - Pints & Pours - Tue 5/5, 6:30pm–8:30pm
Arts & Culture
Cherokee Ranch & Castle - Castle Tour - Thu 4/30, 10:00am–11:30am - $21-$24 - tickets
PACE Center - Lutheran High School Presents: You Can't Take It With You - Fri 5/1 - $10 - tickets
Castle Rock Museum - Castle Rock Historical Society Annual Trolley Tour - Sat 5/2, 10:00am–3:00pm
PACE Center - Denver Ballet Theatre Presents: Don Quixote - Sat 5/2, 1:00pm–6:30pm - $40-50 (Adults $50, Seniors $45, Children $40) - tickets
PACE Center - Reel Stories: AANHPI Voices in Film - Sun 5/3, 3:00pm–6:30pm - $10 - tickets
Lone Tree Arts Center - Step Afrika! - Sun 5/3, 7:00pm - $45-$65 - tickets
Cherokee Ranch & Castle - Arts Afield 2026 - Wed 5/6 - $39 - tickets
Nightlife & Entertainment
Wide Open Saloon - Thursday Line Dancing - Thu 4/30, 6:00pm–10:00pm
Parker Garage - Parker Derby Party - Sat 5/2, 2:00pm–5:00pm
The Parker Hotel - Kentucky Derby Party - Sat 5/2, 3:00pm–6:00pm - $50-$65 - tickets
Sinners & Saints - The Dirty Derby — Kentucky Derby Party - Sat 5/2, 3:00pm–7:00pm - tickets
Family
Castle Rock Museum - Scavenge The Rock — Downtown Castle Rock Scavenger Hunt - Fri 5/1, 8:00am–1:00pm
Rocky Mountain Wildlife Alliance - Rocky Mountain Wildlife Alliance Open House - Sun 5/3, 10:00am–1:00pm
Festivals & Fairs
Sky View Farm - Colorado Nonprofit Mini Derby - Sat 5/2, 1:00pm–5:30pm - Free-$108.55 - tickets
Outdoor & Adventure
Various trails throughout Castle Rock - Spring Up the Creek 2026 - Sat 5/2, 9:00am–11:00am
Castle Rock Library - Basics of Birdwatching Class - Tue 5/5, 6:30pm–7:30pm
East Plum Creek Trail - Basics of Birdwatching Guided Walk (Part 2) - Wed 5/6, 8:00am–10:00am
Community
The Overlook Clubhouse (7853 Piney River Ave) - Prospect Park Neighborhood Watch Training - Thu 4/30, 5:30pm–8:30pm
Alidade Brewing - Rip & Sip TCG Night - Thu 4/30, 6:00pm–9:00pm
The Overlook (7853 Piney River Ave) - First Friday — May Day - Fri 5/1, 5:00pm–6:30pm
HRCA - Community Garage Sale - Sat 5/2
Alidade Brewing - Cinco de Burro at Alidade - Sat 5/2, 11:00am–8:00pm
Teaology Tea Cafe - All Things Spiritual - Sun 5/3, 10:00am–12:00pm
Miller Activity Complex (MAC) - Parks and Recreation Summer Job Fair - Wed 5/6, 3:30pm–6:00pm
On the Horizon
PACE Center - American Academy Presents: The SpongeBob Musical (Castle Pines Cast) - Thu 5/7 - $10-15 - tickets
Cherokee Ranch & Castle - May Vino Voyage: Celebrate the Flavors of Spring - Fri 5/8 - $69 - tickets
HRCA - Mother's Day 5K - Sat 5/9
Gateway Mesa Open Space - Basics of Birdwatching Guided Hike (Part 2) - Sat 5/9, 7:30am–9:30am
Outlets at Castle Rock - Moms & Mimosas - Sat 5/9, 11:00am–2:00pm
PACE Center - Broadway Lights! Recital - Sat 5/9, 11:00am–5:00pm - $23 - tickets
Alidade Brewing - Pop-Up: Blooms & Books at Alidade Brewing - Sat 5/9, 1:00pm–5:00pm
Lone Tree Arts Center - Littleton Youth Ballet Presents: Hansel and Gretel - Sat 5/9, 6:00pm - $6-$42 - tickets
Lone Tree Arts Center - Seedlings: Big Bubble Circus - Tue 5/12
PACE Center - Shaun Johnson: Big Kid Stand Up Tour - Fri 5/15, 7:30pm - $35 - tickets
Highlands Ranch Community Association - Spring Craft Fair - Sat 5/16, 10:00am–3:00pm
Festival Park - Summer Kickoff Concert - Sat 5/16, 5:00pm–10:00pm
Cherokee Ranch & Castle - Princess Party at the Castle 2026 - Sun 5/17 - $51 - tickets
Cherokee Ranch & Castle - Murder & Mystery: Live and Let Die! - Fri 5/22 - $86 - tickets
Cherokee Ranch & Castle - Tequila Tasting at the Castle - Fri 5/29 - $96.95-$98.95 - tickets
Civic Green Park - Highlands Ranch Beer Festival - Sat 5/30, 2:00pm–5:00pm - $40-$55 - tickets
Need more events? Check out https://dougcosocial.com/events
Hometown Headlines
Wildfire Protection Open House Coming May 9
TLDR: With Stage 1 Fire Restrictions in place after a warmer-than-average winter and way below-normal moisture, Douglas County is hosting a free wildfire-protection open house Friday, May 9 to help residents prepare their homes. Open to all DougCo homeowners.
DCSD Considering November MLO to Boost Teacher Pay and Programs
TLDR: Douglas County School District floated a potential $50 million Mill Levy Override at its April 21 board meeting, mostly aimed at teacher pay raises and career/technical education programs. The board will decide in August (after another summer poll) whether to put it on the November ballot. For context: a $50M MLO would cost about $31 per year per $100,000 of home value.
Highlands Ranch Wants Your Take on a New Plaza Drive Park
TLDR: HR Metro District is collecting public input on a proposed new park along Plaza Drive. The online survey is short and open through Friday, May 8.
Calling HR Artists: Colorado 150 Art Contest Open
TLDR: HRCA is inviting artists of all ages and skill levels to submit original artwork capturing what makes Colorado special — mountains, history, community, food, everyday moments. The winning piece will be featured on a limited-edition cup at the August 1 Colorado 150 Celebration.
A Parker Volunteer Just Hit His 2,000th Ride for Older Neighbors
TLDR: Parker resident Bill Monroe, who has volunteered with Aging Resources of Douglas County since 2019, just completed his 2,000th ride helping older residents get to grocery stores, doctor appointments, and recreation centers across the county.
The Juniper Launches Leasing for South Building in Downtown Parker
TLDR: Phase two of the Mainstreet luxury rental development is now leasing — 170 new residences in a four-story building at 11085 S. Pine Drive. The North Building (94 homes) opened last spring and is already 80% leased.
Local partners and occasional affiliate links help support DougCo Drop and keep it free for readers. Send an email to [email protected] if you’re interested in sponsoring the newsletter.
If someone forwarded this to you and you want local updates like this every week, subscribe here! Looking for even more Castle Rock-specific events and stories? Subscribe to our sister newsletter, Castle Rock Crew.
