First “Fun” Halloween

Okay, so this picture may not exactly scream “fun” Halloween, but I promise it was 🙂

I saw that expression, “first fun Halloween” on another mom’s Instagram, and instantly related. Because the first couple of Halloweens with kids are cute and all (there’s nothing more adorable than a tiny costume), but babies can’t walk or eat candy so the whole trick or treating thing really doesn’t work out that well.

This was really our first true Halloween as parents, the first one that felt like all of those things Halloween feels like as a kid, spooky and fun and dripping in chocolate and nougat. I wasn’t really all that excited about Halloween this year, and went into the evening a little skeptical and wary, because well, Ryland is 2. I envisioned meltdowns and costume boycotts and just a lot of tears and frustration.

But then somewhere in that first block of trick or treating, as I held Ryland’s hand and led her from one candy bucket to the next, all of my cynicism and trepidation was replaced by this warm, lovey nostalgia. It felt…magical, the way you always envision trick or treating with your kids will feel long before you actually have children and grow wary of forced holiday “moments.”

We went super early (4pm! hello life with toddlers) to Hanover Avenue in the Fan, which is literally famous for its Trick or Treating. Yet, it also feels deeply personal to me because I moved to that area in middle school and actually went trick or treating there myself (at that awkward stage where you kind of know as you’re trick or treating that you are way too old to still be doing it…). Hanover Ave marked the end of my childhood Halloweens, and so it felt sweetly, perfectly poetic for it to mark the start of Ryland’s childhood Halloweens.

It tends to become a madhouse later on in the night, but in the early evening it was absolutely perfect. The crowds were minimal. Most of the trick or treaters were pint sized. The neighbors were all still cheerful and eager, with full candy baskets. It was a warm, beautiful fall night, with yellow and red leaves all over the sidewalks and that perfect, golden autumn sunlight.


Ryland took a little coaxing at the first stop (for non Richmonders, in the Fan the houses are townhouses and all right next to each other, and on Halloween all of the neighbors on this one street come out onto their stoops, so you don’t have to ring doorbells or anything, it’s literally the perfect trick or treating for toddlers because they can walk two blocks and fill up their candy bucket). But when she realized that strangers were literally GIVING AWAY CANDY, she quickly caught on.


She was so sweet and careful with each piece of candy, wanting to stop and carefully inspect it (or try to unwrap it to eat 🙂 ) before delicately placing her basket on the ground and then placing the candy into the basket.

IMG_1127.jpgFor a solid 2-3 blocks she was really into it.


The decorations were, as usual, absolutely insane. There were so many amazing houses that I sadly didn’t get pictures of, but I loved this Goonies themed one and this Little Mermaid one.



Fairly quickly she decided she would rather ride in her stroller and eat her candy than keep Trick or Treating. But we had fun walking up and down the street and checking out all the cute costumes and amazing decorations. Bobby was a little overwhelmed but seemed to take things mostly in stride 😉


We wrapped things up early, just as the sun was going down and the older Trick or Treaters were hitting the streets, grabbed a super yummy dinner from the new Roots near VCU, and were home by 6:30 (always the sign of a successful night).

Ryland spent the next 2 hours literally bouncing off the walls, which seems kind of essential for a true Halloween experience.

It ended up being a really sweet, low stress evening. I didn’t worry about elaborate costumes (I grabbed this adorable princess/fairy/butterfly dress from her closet, she got it as a gift from my sister in law a few months ago, Bobby’s costume was a $15 second hand steal off of FB, and chosen because it basically was an elaborate vest and incredibly easy to get on and off). The city came through with all of its fall magic and charm, as it always does. And we have our first “fun” Halloween in the books 🙂





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