Portland is the top place I’ve traveled to in the US. From the trendy coffee shops, to the scenic waterfalls and wine country – this city has it all! I love to travel more than anything in the world, but never have I ever loved a city so much that made me second guess my home in Las Vegas.. until I visited Portland.
I went in the fall when all the leaves were falling, which made this city even more of a dream!
If you’re wondering what to do in Portland on a short, 3 day weekend get-a-way, you’ve come to the right place! This detailed guide includes best things to do in downtown Portland, day trips, wine tasting in Wilamette Valley, Waterfalls worth seeing, where to eat so SO much more!
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Where to stay in Portland?
Portland has a bustling downtown area that doesn’t feel like a typical big city. There are not hundreds of people walking the streets, minimal traffic and prices are fair! If this is your first time in Portland, I would highly recommend making the downtown area your hub. You are in the center of all the best nightlife, trendy coffee shops, best restaurants, and a short drive away from beautiful waterfalls or wine country. Click here to view hotels in the downtown area.
My second recommendation would be to stay in the Nob Hill district. It is more quiet with a lot of vintage shopping and wine bars. You may be farther from the famous sites, but the area is really unique. Click here to view hotels in the Nob Hill District.
What to Pack for Portland in the Fall?
Other than my 10 travel essentials I can’t live without, these are my top 3 recommendations for a trip to Portland:
1. Travel size umbrella
It’s no secret that it rains a lot in Portland! It is green for a reason! I bring a travel size umbrella on ALL my trips because it’s so small and fits in my over-the-shoulder purse if I need it. I got mine on amazon for extremely inexpensive and comes in a ton of different colors. Click here for the umbrella I bought!
2. Light Rain coat
It rains almost year round in Portland, so regardless of the season you travel in, I would bring a light rain coat/wind breaker with you that you can easily throw over whatever outfit you’re in. I live in the desert where it NEVER rains, so I bought the least expensive one I could find. Click here for the rain coat I bought!
3. Rain boots
Rain boots are something I didn’t bring but regretted I didn’t. There is a lot of walking in any big city, especially if you are staying in the downtown area. You will want shoes that are waterproof and dry quickly. Click here for an affordable pair of rain boots!
Day 1: Explore Downtown Portland
Again, I recommend staying in downtown Portland because it will make you walking distance to pretty much anywhere! We checked into the hotel and grabbed a quick bite to eat at this adorable restaurant: Bottle + Kitchen.
After your belly is full of yummy lunch and craft cocktails, its time to explore downtown Portland!
First stop of course, Voodoo Donuts! The amount of crazy combinations this place has keeps the locals and tourists coming back for more!
& How cute is my mamma?! She took my pose and made it cuter than I ever could!
Next up, head over to Powell’s Bookstore, located less than a ten minute walk from Voodoo donuts. This three-story bookstore is the perfect place to pick up some souvenirs for back home! So many locals come here, grab a book and spend the day in the coffee shop that’s inside.
Next stop, the Nob Hill district. This was my favorite part of Portland by far! To get there, you will walk through beautiful neighborhoods that are filled with colorful, Victorian-style homes. Nob Hill is filled with wine bars, vintage shops and stylish bistros.
Last stop of the very busy day (hey, you only have three days, you have to make the most of it!) is catching a Portland Trail Blazers basketball game. It was a good break from the cold, rainy weather and was a lot of fun to see! You can check out their game schedule here.
Day 2: Wine Tasting in Willamette Valley
The drive to Willamette Valley is about an hour, making it the perfect day trip from Portland! I wouldn’t recommend driving because on this itinerary, you will get pretty tipsy!
You can hire a driver who picks you up in Portland and can recommend some of the lesser-known wineries. I would highly recommend the company we used: Insiders Wine Tours. We had the owner, John, who was simply amazing but we were his last ride before retirement. His kids took on the family business and if they were anything like John, I am sure you will receive the same great experience.
Stop 1: Arborbrook Vineyards
Arborbrook is a family owned vineyard that specializes in Pinot Noir. This was my favorite winery because we got to meet the owner, Dave, who is a banker by weekday and winemaker by weekend! He filled our glasses while sharing his passion for wine. You can stroll around the vineyards just outside the tasting room, which makes for the perfect photo opp!
There my mom goes again steeling my poses and one upping me, ha!
Stop 2: Aramenta Vineyards
Aramenta Vineyards is a quaint mom & pop winery! We were seriously the only people there – such a hidden gem! The property is beautiful and the wine was delicious, couldn’t ask for anything more.
Stop 3: Fairsing Vineyards
Fairsing vineyards is a much larger winery. It was very crowded, for good reason – the view was second to none!
They have a large tasting room with comfy couches and an outside deck. The best part is the lounge chairs that surround the lawn, giving you expansive views of Willamette Valley.
TIP: I would skip the tasting and just grab a glass of wine. Sit out on the lawn chairs and soak in that view for as long as possible!
Stop 4: De Ponte Cellars
De Ponte is another winery with a great view! They have a patio out back that overlooks the valley. From what I recall the wine was good but after a few hours of tastings, it all begins to “blend” together (ha, get it?).
Day 3: Oregon Waterfall Tour & Flight home
If you take a late flight out, it will give you plenty of time to do a waterfall tour in the morning!
Unfortunately, I went the same year there was a major forest fire so a lot of waterfalls were closed due to mudslides. I am already dying to go back in the summer and spend a full weekend exploring the nature side of Oregon!
There are endless tours to choose from that pick you up in downtown Portland, I would recommend picking one that includes the Columbia River Gorge and Multnomah Falls (the two most popular sights). You can browse pricing and available tours here!
Until next time, Portland!
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