Willamette Valley Bachelorette Party

Bachelorette Weekend Itinerary: Willamette Valley, Oregon + Portland

Janie’s Oregon Trail Before The Veil!

Janie officially ties the knot next month, and we are so excited about the big day! Since Blair and I are the two maids of honor (YAY!), we had so much fun planning the bachelorette party. We wanted to plan a fun girls weekend to celebrate, but also choose a destination that wasn’t TOO rowdy. Half of Janie’s bridesmaids live on the east coast and half on the west. Since her wedding will be in Rosemary Beach, FL, she wanted to celebrate her bachelorette on the west coast to make it easier for some of the girls! Napa was the first place that came to mind, but none of the bridesmaids had visited Oregon, so we knew this would be a fun new experience! We traveled with a total of 10 girls (2 arriving a day later), and we had such a fun and easy experience navigating our way through Willamette Valley!


Since people were flying in from all over the US, we decided to spend the first night in Portland at the Kimpton Monaco.  They have huge suites, so we booked two connecting suites – plenty of space for 8 girls! Also, the Kimpton has complimentary wine and music around 5 PM in the lobby, so this was a fun way for us to ease into the evening.  They surprised us and delivered champagne to our room to kick off the bachelorette! We couldn’t have been more pleased with the hotel choice!

In Portland, we had a blast scootering around town on Limes and Birds to check out the scene.  We highly suggest keeping your schedule open, because there is always a festival or an interesting store to visit.

We had dinner at Departure our first night, which has a really cool ambiance! It’s definitely the trendiest spot we visited in Oregon, and we loved it. Departure is the rooftop bar/restaurant of The Nines Hotel, and they have incredible cocktails, sushi, and small plates.  It was the perfect girls night!

Afterwards we roamed the town for entertainment and checked out a concert at a local bar. It was definitely more of a dive than the hip vibes at Departure, but it was such a fun night! After the bar, we stumbled upon a few interesting dance clubs, and the scene was definitely a night to remember! Exploring the night without a solid plan and agenda was definitely a fun way to explore the nightlife scene! You never really know what you’re going to find, and that’s what made it so memorable.

As the largest city in Oregon, Portland is known for its eclectic culture, local breweries, and diverse food scene. Don’t miss attractions like the International Rose Test Garden, the Portland Art Museum, and the iconic Powell’s City of Books.

Safe to say, you can’t be bored in Portland!  


After a big first day in Portland, we all slept in a little and walked to The Imperial in the Hotel Lucia for lunch.  We all loved the fresh food and it was absolutely perfect to kickstart our day. It was a bit chilly and rainy, so hotty toddys at brunch really hit the spot!  Also, while in Portland don’t forget to check out Stumptown Coffee – this is a must for coffee lovers!

After lunch we walked to Hertz and picked up our rental cars, and we hit the road for Newberg. The drive was super easy and only about 45 minutes to Newberg, and it was really pretty! We loved getting to see more of Oregon along the way – especially passing all of the apple fields near town!  Fun Fact: it’s illegal to pump your own gas at most gas stations in Oregon and could be fined up to $500, as they are all full service – such a surprise!

Where To Stay

Originally we debated booking rooms at The Alison Inn (has a great spa!) or The Atticus Hotel in McMinville, but we decided a house would be more fun and booked the The Pearl House in Newberg. Best decision! The Pearl House was absolutely perfect for our group! The house slept 8-10 people comfortably, and it had tons of spacious living rooms, wrap around porches, two garage spots, and a large outside fire pit.  We could not have been happier with the house or location. It was beautifully decorated and looked straight out of a Restoration Hardware catalogue – swoon!

Since Saturday would be full of wine tasting, we decided to do the lingerie shower around 5PM on Friday night.  While Janie and the girls left for the grocery store to stock up on wine and snacks, we decorated the house, arranged party favors for the girls (read about those here!), and set up an adorable panty line that corresponded to this poem our mom planned with corresponding gifts. If you’re looking for a memorable lingerie shower idea, the poem was so special – Janie even shed some tears from the surprise!

Like we said, we LOVED the location of our house, so we walked to Ruddick Wood Tavern for dinner that night.  You can’t miss this spot! We had a private room in the tavern, and unlike some private rooms in restaurants, this one wasn’t stuffy –  It was loud, had great music, and it even had board games in the room! It felt like we had unlimited wine thanks to the endless carafes, plus the food was phenomenal – duck beignets, steak frites, and so much more. We couldn’t have been happier with our night!

We knew we had a big day of wine tasting on Saturday, so we headed back to to the house after dinner to chill.  Willamette Valley isn’t known for their nightlife, but there were a few cute bars still open, so there would be plenty to keep you entertained.


Thanks to a great recommendation from a friend, we hired Wayne from, A Great Oregon Wine Tour, to be our bus driver, and he was fabulous!!! Since this was our first time to Oregon, Wayne made the whole experience so easy and handled everything for us!  

We shared recommendations from friends who had visited and gave him a list of around 15 vineyards we would be interested in visiting. Wayne planned the logistics, booked reservations, and made sure we would have a nice mix of vineyards. We paid a price per person (which included lunch, all tastings, and transportation), and overall we thought it was a great value.  

The best part about our tour was that Wayne had quite the personality, so you can say it even includes free entertainment! If you visit Willamette Valley, be sure to schedule a tour with Wayne – you will not regret it!

Willamette Valley Bachelorette Party

Archery Summit

Our first stop on our wine tour was Archery Summit.  We sat at a big table outside overlooking incredible views of the valley.  This was the perfect vineyard to kick off our morning, because it was peaceful, quiet, beautiful, and relaxing.  A sommelier delivered each glass to our table and gave us a full introduction to the Willamette Valley wines. We would highly recommend it.

White Rose Estate Winery & Vineyard

Our second stop was White Rose Estate Winery and Vineyard, which was Blair’s favorite.  The tasting room was small and without windows, so it felt like you were somewhat in a wine cave.  We stood at the bar as they poured the wines, so it had a different feel than our first vineyard. However, the grounds at White Rose are OUT OF THIS WORLD.  It’s incredibly picturesque, and we had so much fun running through the vineyards.

Torii Mor

Our third vineyard of the day was Torii Mor, which is where Wayne served us a beautiful lunch with cheeses, meats, and hors d’oeuvres. While the views were amazing and the wine was great, the winery service was not same level as the other vineyards we visited.  However if you’re nearby, you should still drop in!

Beaux Freres

The final vineyard on our wine tour was Beaux Freres, which we loved! This was the most casual vineyard of the day, and we really got to learn so much about the wine and get a firsthand look of how the wine was made. This was the perfect place to end the day, because we sat at a huge picnic table and soaked in the final winery and learned so much about Willamette Valley from the local sommelier and Wayne.  The vibe was very local, and the wine was delicious!

Overall the tour was perfect,  because we had everything from luxury to rustic, and formal to relaxed.  

After-party: Lumpy’s Tavern

THEN THE AFTER-PARTY STARTED.  After a full day of wine-tasting, we decided to have Wayne drop us off at Lumpy’s Tavern. Now the scene at Lumpy’s isn’t where you would expect to find 11 bachelorette party girls, but the dive bar was an absolute blast.  We danced all night to the live band, sang karaoke, indulged in fried food, and our friend, Eliza, even convinced the ENTIRE bar to join us dancing to the Love Train. I highly suggest checking out Lumpy’s – you’re guaranteed to have fun!  We eventually ubered home and called it a day, but from start to finish, the day was perfect.


Half of the group left for the airport early on Sunday, but the rest of us slept in and enjoyed a lazy morning.  It rained most of Sunday, but we had an incredible lunch at Red Hills Market (amazing fresh food) before heading back to Portland.  

​​​​​​​We planned to hike, but the weather did not permit, so we decided to check out Multnomah Falls. Multnomah Falls is about 15 minutes outside of Portland and is the tallest waterfall in Oregon. The views were absolutely stunning!

We also stopped at beautiful Vista House at Crown Point on our way to check out the best views of the Columbia River Gorge!

Since we spent our first night in Portland exploring downtown/the business district, we wanted to check out a different side of Portland for our last night.  We checked into Jupiter NEXT to explore a more local/neighborhood side of the city. Jupiter Next is the new “big brother” hotel of the Jupiter boutique hotel next door.  The hotel was brand new, very insta-worthy, and exactly what we wanted. After driving in from Newberg that morning, we walked all over the neighborhood and checked out cool restaurants. We decided to have a progressive dinner where we would grab a cocktail and small bite at numerous restaurants, which was a fun way to taste our way through Portland. Tusk was such a cute spot, and we HIGHLY recommend eating at Bamboo Sushi!  Bamboo Sushi is a Portland spot with a few locations, and the atmosphere was trendy with great sushi. To round off our night, we popped into the Jupiter hotel to catch a concert at the Doug Fir Lounge. This was one of the coolest concert venues, and you should definitely check it out when you’re in town!


… but wish we had more time to stay, explore! One of the top tourist spots for foodies is Voodoo Doughnuts (warning: there’s always a line!), but if you want to eat like a local, try Blue Star Donuts!


·         Oregon is casual – no need to bring heels! We mainly wore jeans, sweaters, and boots/sneakers

·         If it’s rainy season, plan to bring a raincoat.  It rained a few times while we were there, but it didn’t impact our day. We still had a blast!

·         Oregon is surprisingly affordable! We were pleasantly surprised with the prices, especially with the high quality service and food!

·         Powell’s City of Books in Portland is recognized as the world’s largest independent bookstore in the world, so be sure pop in when you visit!