Plan Your Holiday Activities in Lake Oswego Now (Part 1)

It may not even be Halloween yet but it’s never too early to start booking your holiday festivities in Lake Oswego. Popular events like the Tinseltown Trolley and Holiday Concerts at the Lake Theater sell out early. So start making a list and book the festivities that require reservations.

Luckily there are lots to choose from–so many that I’m covering them over two different weeks. Here’s the first installment.

Bales & Lamb’s Palisades Market Holiday Food and Wine Show. It’s the biggest, liveliest happy hour in Lake Oswego! This annual event is a great excuse for neighbors to catch up over free samples of everything from cheese and wine to eggnog and dessert. Wednesday, November 7 from 4:00 p.m. to 7:00 p.m. Palisades Market, 1377 McVey Avenue. 503.636.2213

Taste of Thanksgiving. Get inspired for your Thanksgiving feast with a chance to sample Zupan Market’s Thanksgiving dinner men as well as holiday beverages, appetizers and desserts. Saturday, November 10 from 11:00 a.m. to 3:00 p.m. 16380 Boones Ferry Road, 503.210.4190.

Holiday Open House. Walk through a winter wonderland while you pick up some ideas for holiday decorating. Check out gift ideas, holiday décor and seasonal inspiration along with hot cider and treats. Thursday, November 15 from 3:00 p.m. to 6:00 p.m. Dennis’ 7 Dees, 1090 McVey Avenue, 503.636.4660.

Lakewood in City Lights. This annual event is returning to downtown Portland to the Sentinel Hotel. Enjoy dinner catered by Jake’s Grill, entertainment, and silent and oral auction. Make a night of it and stay at the hotel at a special rate. Saturday, November 17 from 5:30 p.m. to 9:30 p.m. Tickets are $100/person and can be purchased at the box office, online or by calling 503.635.3901.

Reunion Farmers Market. Local farms bring autumn’s bounty to downtown Lake Oswego. Enjoy shopping in the crisp fall air and pick up some fresh ideas for your Thanksgiving feast. Saturday, November 17, from 10:00 a.m. to 3:00 p.m. Millennium Plaza Park, First and Evergreen.

Horse Drawn Wagon Rides. Here’s another opportunity to slow the season down and take in the sights as enjoy a 20 minute ride through downtown Lake Oswego and the First Addition neighborhood while the Reunion Farmers Market is taking place. Saturday, November 17 from 10:00 a.m. to 3:00 p.m. Limited reserved seating ($8/Adults; $5/Youth) is available on the hour by contacting 503.675.3985. The rest of the seats are first come, first served for rides on the half hour: $5/adults; $3/children. Millennium Plaza Park, 200 First Street.

Lake Oswego Arts Council Holiday Gallery. Finding the one-of-a-kind gift starts here where local artists from all media bring their handcrafted work for you to choose from. The gallery is open for business through December 29 on Tuesdays through Saturdays from 11:00 a.m. to 4:00 p.m. 510 Museum and ARTspace, 510 First Street. 503.675.3738.

54th Annual Tree Lighting Ceremony. Enjoy one of Lake Oswego’s longest standing traditions which includes tree lighting, caroling, treats, and a visit from the big guy decked out in red and white. Friday, November 23 at 5:30 p.m. Begins at Bigelow Plaza on the corner of 5th and A Avenue and proceeds down to Millennium Plaza Park.

Michael Allen Harrison Holiday Show. Popular pianist Michael Allen Harrison returns to Lake Oswego to help ring in the holiday spirit. Monday, November 26 from 7:00 p.m. to 9:30 p.m. Lake Theater and Café, 106 N. State Street. $25/General Admission; Buy tickets online.

White Christmas. It can’t get much more classic than this! Enjoy Lakeridge High School’s rendition of this much-loved story. Performances at 7:00 p.m. on November 30, December 1, 6 and 8 with additional 2:00 p.m. shows on December 1 and 8.

Tinseltown Trolley. It’s Lake Oswego’s version of the Polar Express. Hop aboard and let your imaginations soar as you enjoy carols, story time, treats and more! Friday, November 30 with rides leaving at 3:30 p.m., 4:45 p.m. and 6:00 p.m.; Saturday and Sunday, December 1 and 2 with rides leaving at 1:00 p.m., 2:15 p.m., 3:30 p.m., 4:45 p.m. and 6:00 p.m. Reservations required and tickets sell out fast. Tickets are $19/Adults; $16/Youth 12 and under. 503.675.2549.

Dennis’ 7 Dees Reindeer Magic. Bring the kids to meet Santa and his reindeer. Ticketed admission ($7 for everyone older than one)  gives you access to view and take pictures with the reindeer, ride the holiday train, sit on Santa’s lap, enjoy holiday music and other festivities. There are additional costs for some activities like face painting, food and beverages and professional pictures with Santa.  Tickets are on sale online now until sold out. Saturday, December 1 and Sunday, December 2 from 10:00 a.m. to 5:00 p.m. Lake Oswego Garden Center, 1090 McVey Avenue. 503.636.4660.

Holiday Magic Breakfast Theatre—The Peppermint Bear Show:Who Needs Sneeds? Enjoy a special holiday continental breakfast ½ hour before the curtain goes up for this holiday production featuring area high school student performers. Geared for ages 3-12. Saturday performances are twice daily at 9:30 a.m. and 11:30 a.m. on December 1, 8, 15 and 22 and at 11:30 a.m. on Sundays December 9, 16 and 23 in the Lakewood Center Community Meeting Room at the Lakewood Center for the Arts, 368 S. State Street. Advance reservations are required by purchasing tickets either online, at the box office or by calling: 503.635.3901. Fee: $15/adults; $12/youth 18 and under.

Holiday Gift Show at Oswego Heritage House. Get your holiday shopping done early and local with selections that include hats, jewelry, puppets, wine and more. Wednesday, December 5, 10:00 a.m. to 6:00 p.m. Oswego Heritage House. 398 10th Avenue. 503.635.6373.

Christmas Ships Trolley Excursions. Come see the lighted Christmas ships along the Willamette River from the comfort and warmth of the Willamette Shore Trolley. Schedule begins Wednesday, December 5 with two trolleys running at both 6:30 p.m. and 8:30 p.m. as well as on Fridays, December 7 and December 14 and Wednesday, December 19. There will be one trolley running on Wednesday, December 12 at 3:30 p.m., 6:30 p.m. and 8:30 p.m. Tickets are $30/person. Catch the combined fleet on Saturday, December 15 for $40/person on two trolleys leaving at 3:30 p.m.

Gingerbread House Workshop for ages 6-13. Who needs a boxed kit when you can bake your own gingerbread? Luscher farmhouse Chef Laura Content will help kids bake gingerbread, decorate a keepsake house and send them home with dough to bake. They’ll finish up by making holiday cards. Saturday, December 8 (#18330) from 9:00 a.m. to 12:00 p.m. and (#18337) from 1:00 p.m. to 4:00 p.m. at Luscher Farm, 125 Rosemont Road. $52/Resident; $78/Non-Resident. Register online.

It’s a busy time of year so don’t miss out on what’s happening in Lake Oswego whether you already live here or are thinking of moving to Lake Oswego. Click the “Sign me up” button in the top right hand column and receive weekly updates. And if you’ve got a question—whether it’s about buying or selling a home in Lake Oswego or where’s the best place to find your Christmas tree—feel free to give me a call at 503.939.9801. I’d love to help you out!

About lovelakeoswego

I feel pretty lucky—I live where I work and I love where I live. As a Realtor in Lake Oswego, I get to share that enthusiasm with clients every day. Through this blog, with the help of my freelance writer wife, Genita, I’d like to share that enthusiasm with you. The quality of life you’ll find in Lake Oswego belies its size—there is so much to experience here from a fireworks show over the lake on the 4th of July to the Festival of the Arts--one of the premier arts events in the region. So please check in each week for another reason why I love Lake Oswego and who knows—maybe you’ll fall in love too! If you’re interested in experiencing Lake Oswego personally, please feel free to contact me either on my cell at (503) 939-9801, via email at or check my website by clicking the link in the "Contact me" section in the right-hand column. I would love to show you around.
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