More than 25 skeletons are hanging from lamp posts around Downtown Littleton right now. Each one has an oversized toe tag with a QR code. Scan a tag and you're entered to win a gift card to a downtown business. You can enter up to 25 different skeletons each week. There are $100 drawings on October 10, 17, 24 and 31 and a $250 grand prize on Halloween. The promotion is called Bones About Town. It's also a good sign of how Halloween works on Main Street. Downtown Littleton's October isn't one big event. It's a month of small ones, and most of them are put on by the shops and restaurants.
That changes how you plan. One trip downtown on a Saturday afternoon only shows you a small part of it. If you know which night belongs to which business, you can get to almost everything. Most of the schedule below comes from the Downtown Littleton October roundup published October 6, 2026, along with the individual event pages it links to.
Two long-running traditions
Two traditions have been around long enough that everything newer fits in around them.
Reinke Brothers' Haunted Mansion has been part of Downtown Littleton Halloween for more than 50 years. Reinke Brothers is also a costume shop, so you can pick up a costume and walk through the mansion in one stop. If the full scare is too much for younger kids, there's a "lights on" tour.
Haunts of Littleton is in its 24th year. It's a walking tour that takes you through downtown's streets and alleys after dark. Guides mix local history and eyewitness ghost stories with what the organizers call "tongue-in-cheek muses." Each tour lasts about an hour. They run 7 to 9:30 p.m. on October 16, 17, 23 and 24, with 10 tours a night. Tours meet at the RTD Littleton/Downtown Station at 5777 S. Prince St. The organizer is Friends of 444. Tickets are sold at hauntsoflittleton.com.
Because the tours start at the light rail station, you can take the train in and skip looking for parking on a busy Friday night. Ten tours a night across four nights adds up to 40 departures for the whole season. Pick your night early.
Every night has its own thing
The shops have spread their events across the week, so they rarely compete with each other. Here's the regular schedule for October:
| Night | Where | What's happening |
|---|---|---|
| Wednesdays | Tonic Zero Proof Bar | Craft and movie nights, with alcohol-free drinks |
| Thursdays | Tonic Zero Proof Bar | Horror movies and spooky trivia |
| Fridays, Oct. 9, 16 and 23 | Little Man Ice Cream | BOO-NGO, 6 to 8 p.m. |
| Fridays and Saturdays, Oct. 16 to 24 | Downtown streets | Haunts of Littleton tours, 7 to 9:30 p.m. |
| Any day, all month | Lamp posts districtwide | Bones About Town skeleton scanning |
BOO-NGO at Little Man Ice Cream is bingo with a Halloween theme. Prizes include free Monster Sundaes, and costumes are encouraged. Little Man is at 2449 Main St. The Friday schedule pairs well with the ghost tours. On October 16 and 23, a family can play bingo until 8 p.m. and still make a later tour from the station.
Outlanes Pinball runs its own schedule. Fall League starts today, October 7, with free entry, coin drop and a prize pool of at least $1,000 sponsored by Outlanes. Members get free play on October 15 and 25.
There's also a quieter option. Five Wellbeing Spa has an October package with the Inhale Salt Lounge, Exhale Sound Lounging, a 60-minute massage and a 60-minute facial for $299, down from $319. It's good for Monday through Friday appointments booked and used in October. Spell Books offers a Tarot 101 class, and in-person tarot readings are available at Tonic Zero Proof Bar and iN-TEA.
The dated events, October 10 to 25
On top of the weekly schedule, a handful of one-time events fill the next two and a half weeks:
- Saturday, October 10: First Bones About Town gift-card drawing. A few miles away, the Littleton Museum at 6028 S. Gallup St. holds its Harvest Festival the same day.
- Sunday, October 11, 11 a.m. to 1 p.m.: Pumpkin Painting Party at Little Man Ice Cream. A ticket covers a pumpkin, paint, supplies and a kids' scoop. Pumpkins left at the shop are entered in a community contest, and the winner gets an Ice Cream Social for six.
- Wednesday, October 14, noon to 8 p.m.: Halloween open house at the Uptown & Country boutique. Wear Halloween fashion and you're entered to win prizes.
- Friday and Saturday, October 16 and 17: First weekend of Haunts of Littleton.
- Friday and Saturday, October 23 and 24: Second and last weekend of Haunts of Littleton. On Saturday the 24th, Tonic Zero Proof Bar hosts a spooky slumber party with a murder mystery.
- Sunday, October 25: Goblin Giveout, a daytime trick-or-treat in Downtown Littleton organized by the Littleton Merchants Association. Kids in costume go from shop to shop and restaurant to restaurant, and local merchants hand out candy. The roundup also points families to Little Man's Halloween photo setup and its Monster Sundae.
Check the Goblin Giveout start time before you go. The event page lists 12 to 4 p.m., and the Downtown Littleton roundup says 1 to 4 p.m. If you're bringing small kids, plan on the later time so you're not waiting outside a shop that hasn't started yet.
October 29 to 31: the busiest stretch
The last three days of the month have the most going on. From Thursday the 29th through Halloween night, at least five businesses within a few blocks of each other host something:
- Thursday, October 29: Outlanes Pinball hosts a ladies tournament and costume contest.
- Friday, October 30, 7 to 9 p.m.: Little Man Ice Cream's third annual Monster Mash Costume Ball, with music, trick-or-treats, Monster Sundaes and face painting. The costume contest starts at 8 p.m., with prizes for cutest, spookiest, most original and best group costume.
- Saturday, October 31: Outlanes holds a Halloween Costume Tournament. Tonic Zero Proof Bar has a Halloween party. Ned Kelly's starts its Halloween night at 9 p.m. with live entertainment, drink specials and a costume contest.
- Also on Halloween: the $250 Bones About Town grand prize is drawn.
The Halloween night lineup covers a lot of ground. A household can split up and still end the night in the same part of town. Kids can go to Little Man on Friday, pinball players can go to Outlanes, people skipping alcohol have Tonic, and Ned Kelly's runs late.
If you're on a costume hunt this late in the month, Reinke Brothers is still the downtown stop for costumes and the Haunted Mansion.
A new stop on Main Street
Downtown Littleton has a new shop this fall. Leaves on Main, at 2699 Main St., held its grand opening September 5, 2026. It sells houseplants, handmade pottery, gifts and home decor. Between a pumpkin-painting morning and a Goblin Giveout afternoon, it's an easy place to stop for anyone looking for a fall plant or a hostess gift for the holidays. You can see more at leavesonmain.com.
After Halloween: November on Main Street
Once October wraps up, the holiday calendar fills in the same way:
- Friday, November 20: Pink Friday in Downtown Littleton.
- Friday, November 27, 5:30 to 7 p.m.: the City of Littleton's Candlelight Walk, a downtown parade and holiday gathering.
- Saturday, November 28: Small Business Saturday, organized by Historic Downtown Littleton.
- Sunday, December 13, 5 to 8 p.m.: Holiday's Evening at the Littleton Museum.
The Candlelight Walk is on the Friday after Thanksgiving and Small Business Saturday is the next day. That's two downtown events back to back, much like the end of October. If you have family visiting for the holiday, you can plan both days around Main Street. The Downtown Littleton events calendar is the place to check for details as November gets closer.
I live and work in the south metro area, and October on Main Street is one of my favorite times to be downtown. Whether you're coordinating a move around the holidays, wondering what your home might be worth before spring, or just want to talk through what's next, I'm happy to help. You can learn more about the area on my Littleton neighborhood page or reach out to Jaclyn Broesel. Let's Connect.
