Portland Holiday Checklist
As a Portland native and local realtor, my new-to-the-area clients often look to me for recommendations—where to eat on date night, what events to take the kids to, etc.—and I’m always more than happy to share a few of my favorite local secrets. When it comes to holidays, though, I have way too many tips and tricks to cram all of them into one email. So here is Tessa Gold’s guide to having the best holiday season in Portland, including some of my own family traditions as well as a list (with links) of my favorite PDX winter events, tree farms, and more!
In my family, Christmas begins the day after Thanksgiving when we head to our favorite farm to pick out our Christmas trees. No, the ‘s’ on ‘trees’ was not a typo, we get two or three trees every year—one goes in the foyer, one is set up beside the fireplace for Santa to visit and if I’m feeling super festive, I may even grab a small tree for the kids’ playroom. Friday morning, after the Thanksgiving coma has worn off, my husband, my kids and I get all bundled up in our winter coats and rain boots on, ready for any weather and for our annual family photo at the tree farm. Every year I wear my festive and functional red Hunter boots and every single year the same crazy chicken at the farm goes bonkers attacking my feet until the owners come and pull her off of me. Somehow, this never stops me from wearing the boots. This chicken is notorious for attacking people with bright shoes or boots on according to the owner. It’s now an ongoing joke (and only slightly traumatizing for my children) and I find myself in “ ready judo position” while heading back towards the lodge where we pay for our trees. It’s all part of the holidays, right?
Once we get the trees up, it’s time to kick off the three-day-long process of bringing Christmas to life in our home. Most every room in our home must be transformed into a festive environment of garland, lights and wreaths. My husband frequently leaves the house for multiple hours at a time during these days as he says I get this glazed over look in my eyes and become non-responsive to most any communication he attempts to have. Maybe I become a Christmas zombie, is that a thing? After countless hours of decorating and a few blown circuits, it’s clear that Christmas has arrived at our house. One of my family’s favorite items to bring out of the holiday storage bins is our beloved Elf on the Shelf, Sausage. I might be crazy about holiday decorations, but my husband goes nuts with that elf. Sausage can be found taking selfies with our sleeping children at night and pulling off crazy stunts around the house during the day.
Another Gold family favorite is throwing our annual Gingerbread House decorating party for the neighborhood. It is so important to us to be involved in our immediate community and foster relationships with our neighbors. Our kids always have a blast eating candy and spending time with their friends. I don’t even mind that they usually end up getting frosting all over the house. It’s just such a special tradition for us and something that we will continue to do for years to come.
On Christmas Eve, we round up both sides of our family at Hunan Pearl, our favorite Chinese restaurant in Lake Oswego, followed by the most outrageous white elephant gift exchange you’ve ever been to. My parents scheme all year trying to come up with the most shocking gift imaginable to bring to the party. A few years ago, my grandma accidentally severed the top of her pinky finger in a trunk slamming accident. Attempting to save it, my mom put the top of the finger in the freezer. Unfortunately, it wasn’t able to be re-attached, so my mom kept the finger tip frozen (it was placed nicely beside the kids Dino chicken nuggets) and wrapped it up as her white elephant gift. Yes, we are full blooded Italian, no we are not the mafia and regularly do not keep body parts in the freezer. If you’ve ever seen a more insane white elephant gift, I need to hear about it because this one blew everybody’s socks off (or their gloves-haha).
While I love to share my family’s traditions, I am also a huge advocate for creating your own traditions and memories. The holidays are such a perfect time to invest in your family and your local community. I’ve got a few suggestions to get you started, but I can’t wait to hear about how you take them and make them your own!
My Favorite Local Tree Farms
Sleigh Bells - Located off HWY 99 in Sherwood this farm is known for it’s eccentric holiday gift shop including the most extensive collection of Christmas tree ornaments around.
23855 SW 195th Pl.
Sherwood, OR 97140
Frog Pond Farm - Knock out your pictures with Santa while you hunt for the perfect tree at this family friendly Wilsonville farm. Don’t miss their animal exhibit or toy/farm store either.
2995 SW Advance Rd.
Wilsonville, OR 97070
Lee Farms - You’ll love the service at this Tualatin farm. They’ll cut, shake, and bale your tree and even install a stand and load it up on your car - all while you enjoy a hot, fresh apple cider donut and browse through the farm store.
21975 SW 65th Ave.
Tualatin, OR 97062
Redland Family Farm - Exclusively open Dec. 1st & 2nd, this Oregon City farm offers the full Christmas experience with free hot beverages and s’mores plus free wagon rides, petting zoo, bounce house, visits with Santa, and so much more.
19400 S. Redland Rd.
Oregon City, OR 97045
Need Someone to Put Up Your Christmas Lights?
Shine Forth Enterprises (503) 650-8460
Dan the Window Man (971) 338-0002
My Favorite Family Photographers
The holidays are an awesome time to update that family photo on the wall (or your lock screen). We send out christmas cards to friends and family all across the country each year. The christmas cards we receive are placed on the kitchen cabinets in rows and by the time we ring in the New Year, we usually can’t see most of our cabinets because they are completely filled with beautiful christmas cards from those that we love. Check out these talented ladies—you can’t go wrong with any one of them!
Support Local Businesses this Holiday Season
I’ll be the first to admit that most of my holiday shopping gets done on Amazon these days, but I also love going out and supporting my favorite local businesses. These are some of the cute places I’ve found and fell in love with in and around Lake Oswego.
Adorn - With four locations in the Portland area, Adorn is the perfect place to pick up a new holiday dress for that party on Friday or a cute sweater to gift to your sister-in-law.
Wishbone - One of my all-time favorite places to go for home furnishing and decor, whether it’s for my own house or for staging.
The Grove - This trendy maker’s market located off Lakeview Blvd. sells locally crafted art, clothing, jewelry and more.
Mapel Boutique - Located in West Linn & at Bridgeport Village, this boutique is another local gem perfect for picking out Christmas gifts or treating yourself.
Evereve - Located at Bridgeport Village, this boutique is filled with darling apparel and jewelry items. *(Sarah is who I shop with on a regular basis.)
PDX Holiday Events You Don’t Want to Miss
My Favorites in the Lake Oswego Area
Holiday Events at Bridgeport Village - If you are looking to stay close to home and experience the magic of the holiday season in a family friendly environment this is for you. Our favorite local shopping center holds a wide variety of holiday events from Santa’s Arrival Party to a Nutcracker making craft workshop and more!
Christmas Lights in the Westlake Neighborhood - Don’t want to drive downtown or pay to see a beautiful display of Christmas lights? The Westlake neighborhood in Lake Oswego does an excellent job of decorating every year.
Downtown Portland & Beyond
Zoo Lights - This annual event and the Oregon Zoo is something every local has to experience. With over a million and a half lights and plenty of animals to visit, your whole family will enjoy wandering the zoo at night. Take a ride on the train or grab a bite from one of the delicious food carts while you’re there.
Pioneer Courthouse Square Christmas Tree Lighting - Kick off the Christmas season on November 23rd by attending the 34th Annual Tree Lighting Ceremony downtown. This event includes live music and a 75 foot Douglas Fir tree.
The Nutcracker Ballet - The Oregon Ballet Theater puts on a spectacular rendition of this beloved Christmas classic.
The Grotto - The Christmas Festival of Lights is the largest Christmas choir festival in the world. This a walk through light show with a petting zoo and choir concerts held in the chapel.
Peacock Lane - Visit Portland’s Christmas street on foot or by car beginning December 15th. You don’t want to miss out on the incredible light displays on these homes. Note that there are some pedestrian only nights and driving traffic can be very dense.
The Singing Christmas Tree - Two hours of holiday music performed by a massive choir of all ages. Enjoy a living nativity, fun dance number, and lots of Christmas music, both contemporary and classic.
Lights at the Portland International Raceway - Open November 23rd - December 26th, you don’t want to miss this spectacular drive through light show known as the largest West of the Mississippi. Note the special event dates (such as Bike the Lights) when cars are not permitted.
Christmas Tea at the Heathman Hotel - Enjoy a full Tea Service surrounded by beautiful Christmas decorations. Reservations must be made at least 48 hours in advance.
Cosmic Tubing at Mt. Hood SkiBowl - Fun for the whole family! Spend an evening in the snow complete with music, LED lights, black lights, and more.