Best Organized Trick-or-Treating Events in Richmond

To hear my dad tell it, on Halloween night, they used to grab a sheet, cut out some eye holes, then head out into the dark for a night of trick-or-treating without a parent in sight. When I hear this, my heart stops – as much for the lack of costume preparation and planning as for the lack of parental supervision. I may not have my priorities in order, but I take Halloween seriously.

And I’m not alone. These days, we tend to spend a fair bit of time – and money – getting our kids ready for Halloween. And with good reason. There’s nothing cuter than a tiny, toddling bumblebee or a pint-sized princess. But the main point is that it can sometimes feel like we spend more time getting ready for Halloween than actually doing it. And if you happen to live in a neighborhood or area that isn’t conducive to trick-or-treating for whatever reason, you might find yourself frustrated by a house full of kids in costume with nowhere to go.

With that in mind, we decided to take a look at some of Richmond’s trick-or-treating opportunities, both before Halloween and on the 31st. Not only is it nice to get out and about before Halloween and give those costumes you worked so hard to put together a trial run, but it’s also nice to know that you have a safe, contained environment for your kids. So whether you’re looking for pre-Halloween fun, or just want to try trick-or-treating in in new territory, organized events that offer trick-or-treating can make the Halloween experience that much more fun for everyone.

Fortunately, there are a number of organized trick-or-treating events throughout the Richmond area that will not only give you a chance to take your kids out in all of their costume finery, but will also promise safety, structure, and fun for the whole family.

We’ve taken a look at some of the area’s best organized Halloween events to bring you six of favorites. To make our top six list, each event had to offer:

  1. Safety
  2. Inclusion for all ages and groups, while remaining kid-friendly
  3. Plenty of trick-or-treating opportunities

What we found is events, from formal to informal, that offer a little bit of structure to your Halloween trick-or-treating experience. And because they don’t all fall on Halloween, chances are you can make it to more than one and keep the Halloween fun going for days. But even more importantly, with Halloween falling on a Wednesday this year, you may find that it’s easier to keep your midweek schedule in place (i.e., NOT give the kids copious amounts of candy on a school night). These events offer plenty of opportunities to make the most of Halloween – even if it’s not on the 31st.

Please note that we’ve listed all events in chronological order so that you can plan your Halloween fun from this weekend, all the way up to Halloween day itself.

If you know of a great trick-or-treating event that we may have overlooked, let us know. We would love to hear about it at


Taylor’s SpookieFUN Fest

Trick-or-Treating Spookie FunFest 1 (1)
Pole Green Park / Facebook

Friday, October 19, 2018 at Pole Green Park (Hanover)
Saturday, October 20, 2018 at Poor Farm Park (Hanover)
5pm – 8:30pm

In case you don’t know Taylor, he’s the furry-faced – and oh so lovable – mascot of the Hanover Parks and Recreation department. And this year, on October 19th and 20th, he’ll be hosting some pre-Halloween fun at two of Hanover’s favorite parks. Bring the kids out in their Halloween best for a night of fun that goes above and beyond trick-or-treating. And while there will, of course, be plenty of candy at the event’s trick-or-treat booths, there will also be rides, DJ Luke in the Monster Mash Dance area with a special performance by the Richmond Urban Dance group, inflatables (designed for ages 3 – 12), the Mystery Machine, a Pumpkin Walk, Taylor’s mini-pumpkin patch where you can decorate your own pumpkin, SpookieFUN games, The Game Patrol, Casper’s FUN Hunt & Maze (ages 4 and under), a Flashlight Candy Hunt (ages 5- 12), and more. And to make this event even more enthralling for the kids, Taylor is bringing along a some of his favorite superhero friends, along with Elsa, Anna, Belle…and more! The only catch is that most rides and activities are designed for kids 12 and under – so the teenagers might not like it as much as the little ones. (But, hey, do teenagers really like anything?)

Why we love it: Forget sullen teenagers, we love this event for so many reasons and that’s all that matters. First of all, it’s free (although there will be some candy and concessions for sale). Secondly, it’s offered on two nights, so if crazy family schedules keep you from making one, you can always make the other…or both! Last but not least, SpookieFUN Fest recognizes the need for age-appropriate events that will keep everyone happy and safe. By breaking different events into different age groups, they help you to ensure that your kids will have a safe, fun experience regardless of their age.

Friday, October 19
Pole Green Park
8996 Pole Green Park Lane
Mechanicsville, VA 23116

Saturday, October 20
Poor Farm Park
13400 Liberty School Road
Ashland, VA 23005


Trick or Treat Street

Trick-or-Treating Trick or Treat Street 3 (1)
University of Richmond’s Trick or Treat Street / Facebook

Sunday, October 21, 2018
11am – 3pm

Now in its 20th year, Trick or Treat Street (or TOTS as it’s also known) has become a Halloween tradition for many in the Richmond community. Every year, costume-clad University of Richmond students welcome hundreds of kids (and their families) for a day of activities, food and family-friendly fun. While this Halloween celebration falls more than a week before Halloween, chances are you won’t even notice thanks to the festive Halloween atmosphere, games, decorations and more. For an event that just seems to get better every year, this year’s event promises not to disappoint with a straw maze, bounce houses, train rides, and a petting zoo, as well as tons of games, crafts, and of course, lots and LOTS of candy.

Why we love it: Hmmmm…where should we start? Although geared towards kids 10 and under, Trick or Treat Street is fun for all ages. First of all, the University of Richmond campus is one of the most beautiful spots around – especially on a pretty fall day. Secondly, with activities that go far beyond candy, so it’s easy to distract sugar-obsessed little ones. Plus, this event is free (with requested donations) and it’s open to the entire community. But the real clincher is the purpose behind it.

Aside from simply providing a fun, safe trick-or-treating environment, Trick or Treat Street actually exists as a charitable endeavor. In lieu of admission, families are asked to provide donations. In the past, University of Richmond students have collected non-perishable food items for a local food bank, but for the second year in a row they’ve teamed up with the Ronald McDonald House Charities (RMHC). For their 2018 event, they are asking families to make a $5 – $10 donation that will go directly to RMHC to help them continue their amazing work in the Richmond area, and across the nation.

Stern Plaza (The Quad in front of Jefferson Hall)
University of Richmond
28 Westhampton Way
Richmond, VA 23173


Gayton Crossing Pumpkin Festival

Gayton Crossing Pumpkin Festival / Facebook

Friday, October 26, 2018
5pm – 7pm

It may not have “trick or treat” in the title, but that doesn’t stop the Gayton Crossing Pumpkin Festival from being one of our favorite trick-or-treating events by far. Gayton Crossing, a popular shopping center in the far West End, has been hosting this Halloween event for more than 20 years – and we’d say they’ve got the formula down. Not only will Gayton Crossing merchants be handing out candy to your eager trick or treaters, but a few local heroes will be on hand, as well. This year’s event includes a special Henrico Police Halloween Celebration, a Henrico Fire Truck interactive display, live performances from West End Academy of Dance, and plenty of meet and greet opportunities with some of your favorite local mascots like Rompy, Bubbles, and more.

Why we love it: Gayton Crossing Pumpkin Festival provides a safe place for kids to fill their candy buckets, but it’s actually fun for parents, too. Free and open to the public, the event focuses on family-friendly activities, but is set among shops and restaurants that are fun to browse while the little ones take their five-millionth turn in the bounce house. And because it doesn’t happen on Halloween, you can still trick or treat in your own neighborhood on Halloween night…or better yet, hit up one of our other favorite trick-or-treating events!

Gayton Crossing Shopping Center
9782 Gayton Road
Henrico, VA 23238


Halloween Hoopla at the Children’s Museum

Trick-or-Treating Halloween Hoopla 1 (1)
Children’s Museum of Richmond / Facebook

Saturday, October 27, 2018
2pm – 6pm

Consider this your Halloween dress rehearsal. Held on the Saturday before Halloween, Halloween Hoopla at the Children’s Museum downtown combines all the excitement of a festival and trick-or-treating into one fabulously fun, safe event. Suited especially for little ones, this annual event features monster puppet shows, pumpkin experiments, glitter tattoos, pumpkin decorating, games, prizes and more. But the real highlight is “real-life” trick-or-treating at the museum’s kid-sized replica of a Fan neighborhood. Plus, you’ll have access to all of the other interactive elements, exhibits and displays that makes CMoR a favorite destination for parents and kids alike. And because it’s entirely indoors, the kids can run and play without sending you into a panic. While Halloween Hoopla does require tickets, kids’ admission it totally free and adults are only $4. To get tickets, order online up until 10am the day of the event, or purchase them at the door.

Why we love it: Trick-or-treating with little ones is a mixed bag at best. Some kids want to run to every door and grab as much candy as their grubby little hands can hold. Others decide that NOW they want to be shy and refuse to leave your side – and if you’ve ever had to stand there as a grown adult and ask for candy, then you know how humiliating it can be. Needless to say, it can take a few years to get it all down. Halloween Hoopla is the perfect training ground. The kiddos can wear their costumes and have an authentic trick-or-treating experience through the CMoR “neighborhood” – and if you have some etiquette to work on? Teach some trick-or-treating do’s and don’ts on Saturday, and by the time Halloween night rolls around, you and your kids will be pros.

Children’s Museum Downtown
2626 West Broad Street
Richmond, VA 23220
(804) 474-7000


Trick-or-Treating Squirrel o Ween
Flying Squirrels Baseball / Facebook

Wednesday, October 31, 2018
5pm – 8pm

Squirrel-O-Ween is an annual event that invites the entire community to the Diamond for hayrides, trick-or-treating, games, costume contests, and much more. Hosted by Richmond’s favorite hometown team, The Flying Squirrels, Squirrel-O-Ween promises fun for all ages…from the little ones all the way up to mom and dad. With festivities that spread from the parking lot to the field itself, Squirrel-O-Ween offers family-friendly activities that ensure no one sits on the bench. So don your Halloween best and bring the entire family out for a night of trick-or-treating that they won’t soon forget.

Why we love it: If you’ve ever been to a Flying Squirrels baseball game, then you already know the excitement and energy that fills The Diamond on game day. From cheering fans to exciting plays, kids of all ages love game day. So why not bring that same fun and excitement to Halloween? Not only can you ensure a fun, safe environment for your little trick-or-treaters, your older kids will have a blast, as well.

The Diamond
3001 N Boulevard
Richmond, Virginia 23230


Halloween on Hanover

Halloween on Hanover Ave / Yelp / photo by Follow My F

Tuesday, October 31, 2018
Starting around 5pm or dusk

Over the years, this annual trick-or-treat extravaganza has become the stuff of Halloween legend in the Richmond area. So it’s no wonder that it has topped our list for favorite trick-or-treating events two years running. Of course, it would be one thing if we were the only ones who thought it was amazing. But even the Wall Street Journal has recognized Hanover Avenue as one of the nation’s best places to trick-or-treat. And if you’ve ever hit Hanover Avenue on Halloween, then you’d be hard pressed to argue.

While this is not technically a formal event (only in that it’s not sponsored by an outside organization), it is a grass roots effort of note. Every year, the residents of Hanover Avenue, from about the 1900 block to the 2200 block, try to outdo one another with decorations, effects and all-around Halloween fun. There will be parties. There will be music. There will be a pirate ship. But most importantly, there will be a festive atmosphere, more candy than your kids can carry, and sights and sounds that will entertain everyone in your family – from teens that are too cool to dress up anymore right down to your candy-crazed toddlers who can’t believe you’re actually letting them stay up this late.

Why we love it: When it comes to giant street parties, Hanover Halloween is the mother of them all. But what really sells this trick-or-treating event is that fact that it’s free, safe, and fun for all ages. Plus, the streets are blocked off, which means that even if you end up having to chase a toddler jacked up on fun-sized Snickers, you won’t have to worry about cars…which is always a bonus. With that being said, when we say that these guys go all out, we’re not kidding. That means that there will be smoke machines, animatronics and some scary sights – and portions of it may be a lot for little ones. But if there’s a section that’s a bit too much, just move down the block a bit and let the party carry on.

1900 Block of Hanover Avenue – 2200 Block of Hanover Avenue
The Fan, Richmond

For even more family-friendly Halloween fun, be sure to check out our Halloween Guide 2018: Not-So-Scary Halloween Events in Richmond.