Posts in Adventures
When in Portland! 5 Places I Always Stop at When I'm Visiting
Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

I love being back in the PNW for mannyyy reasons that's for sure, but one of my favs is being able to hop in my car and drive whereverrrr the road may take me. Now don't get me, weekend getaways are totally possible in NYC and something I did take advantage of quite a bit, but being able to hop in your own car and just drive?! That feels dang near magical to me after so many years without a car -- 7 to be exact. So now that I'm back on the west coast I'm basically a born-again 16-year-old who just got her license and I'm still loving every second of it even a year later.

One of my favorite places to adventure to over the years has always been Portland, and now that it's a mere 2.5 hours away (traffic cooperating) you will certainly find me roaming my old hood quite a bit more. And can I please tell you... I swear every time I visit, the city gets a little cooler. Now I know some of the lifers might disagree with all of the growth Portland has had in the last decade, but personally, I love it. So much so, that if I didn't promise my Mom that I'd never move out of state again that I def wouldn't rule out moving south again. 😜#realtalk

So what is it about Portland that is so great? To me, it's a great sized city that has the amenities of big-city living, while still not feeling overwhelming and not being totally terrifying to drive in if you don't know where you're going. Plus it has an amazing food scene (you know me!), arts, culture, and it's still very walkable and accessible. I also happen to know some super awesome people down there so it always gets some extra bonus points for that too! The vibe in Portland is just really great and I only think it has gotten better with time. So that being said, what the heck are my fav places to visit when I'm there? Well today I'm sharing some of my must-visit spots no matter how short of a trip I'm on, which this weekend was less than 36 hours. 

Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

Pine State Biscuits

If there is one place I pretty much always visit when I'm in town (and take everyone I'm visiting with to) it's Pine State Biscuits. Truly this place is heaven on a biscuit and the onlyyyy place around that I would wait an hour in the rain for. And trust me, when I lived in NYC we didn't wait on places and I've liked to stick to that mentality, but Pine State.. Oh I'll wait. Kathy originally introduced me to Pine State at least 10 years ago after seeing it featured on Diners, Drive-Ins, and Dives when they just had a little hole in the wall spot off of SE Belmont and I've been ordering everything off the menu ever since at their now 3 larger locations + their spot at the Farmers Market. At this point I have a few go-tos, although occasionally I'll branch out, or let's be real, someone I'm with will order something else and I'll sneak a bite or two. It's hard to venture from my favs though because they're just THAT good. So what are my go-to's? I'm talking about the McIsley, the Pine State Fried Club and the Reggie Deluxe when I'm feeling real indulgent.

Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting
Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

Powell's Books

Is it even a Portland trip if you don't stop by Powell's? Not in my books. Get it?! I'm a funny one... I, along with a million other people, have such a soft spot for this bookstore. It hails that it is the largest independent new and used bookstore in the world and even if it wasn't I'd still love it. The bookshelves in here just go on and on and on and I love everything about it. One of my favorite things to do when I lived in Portland (and now when I visit) is to wander the halls and find a little corner in the astrology section and check out alllll of the books. Seriously.. I used to spend hours here. It doesn't matter what kind of book you're looking for either, they're going to have it and the best selection at that. Plus they have some really awesome events take place there and all and all it's just a rad place to spend an afternoon.

Voodoo Doughnuts

Now back to food, because, well you know who's writing this right!? Another one of my favorite places to stop when I'm in Portland (or Eugene if I'm catching a Ducks game) is VooDoo Doughnuts. You can find a lot of good donuts on the west coast, sorry east coast but we win at this... and VooDoo sits at the top of my list. If you're interested in some of the other great options locally as well, Little Duck did an awesome Portland Donut Crawl blog post that's worth a read too! Personally though, if I had to only pick one, VooDoo it is. I just love the novelty and the just delicious, fun and not overly fancy flavored donuts. Solid deliciousness. Insider tip too, if you want to stand in line foreves hit up the location downtown, but if you want to get in and out with a box full of your favs and a cute Instagrammable wall then you need to hit up their NE Davis VooDoo Doughnut Too location.

Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting
Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

NW 23rd Ave in the Alphabet District

Awww my old neighborhood! I mean I don't want to brag, actually yes I will brag for a sec, I've been pretty darn lucky to live in some of the best neighborhoods in the cities I've lived in. NW Portland, The Upper East Side in NYC, and the Stadium District in Tacoma. Heck yes! And this neighborhood, well it's truly one of my favs because it is just so stinking cute! I lived off of NW 23rd Avenue in the Alphabet District and it's one of my favorite places to spend an afternoon. When I moved there my mom called it her "happy place" and it's def still makes my list as well. Adorable shops, delicious food, and bars galore.. like what more do you need?

Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

NW 21st Ave is a close second too being just a few avenues over too. A greattt option for nightlife too. So many fun memories and truly something for everyone! Some places I definitely always love to stop at are Saint Cupcake -- their mini cupcakes are to die for! One of the McMenamins locations for some cajun tots and Ruby beer and maybe even an extra stop at their bottle shop that's now open at the end of the ave to grab some Ruby to go too! Pssttt, we're actually getting our own McMenamins in Tacoma in 2019 and this girl is PUMPED to have one of my favorite Oregon spots so close! Wherever you go over here you really can't go wrong!

Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting
Anna Osgoodby Life + Design : When in Portland! 5 Places I Always Stop at When I'm Visiting

Pearl District

Last but not least, another one of my favorite neighborhoods to wander is the Pearl District. After a trip to Powell's of course! (It's nearby) I'm such a sucker for repurposed factories and industrial vibes mixed with new construction and the Pearl combines all of that. Pair that with great options for Happy Hour, art galleries and some seriously amazing food and it has me feeling a little fancy! I worked at the neighborhood Safeway while finishing up college and just fell in love with the neighborhood from day 1 and it has only expanded and grown since. So many fun places to visit and it's just a cool pocket of the city.

Now of course, there are SO many more incredible things to do, see and eat in Portland that I could write for dayssss about but these are just a few of my favs that I always try to make it to. If you have some other recs or places you think I'd like definitely drop a comment below!

To NYC and Back Again
Anna Osgoodby Life + Design : To NYC and Back Again

I moved to NYC Labor Day weekend in 2010 with 5 suitcases, my pup, and my eyes wide for an adventure. I was 21, a year out of college ready to make a bet on myself. I promised my parents I'd only be moving back east for a year, but then years 2, 3, 4, 5 and 6 quickly passed by. Now, a month shy of my 7-year anniversary it's time to say goodbye. Despite not always being New York City's biggest fan, it's always been pretty good to me, so closing this chapter certainly feels bittersweet.

When I first arrived, I was hooked on the energy and ambition of the city. Empire State of Mind was the ringtone on my phone and I was determined to be one of the ones who "made it here". New York was never a dream of mine, but rather an opportunity that fell into my lap. It came knocking twice that year, and on the second knock, I decided it was a sign I should give it a shot. I had only visited twice and didn't know any of the neighborhoods, but I had a job and a boss who helped me get settled. I was naive of so many things, but the one thing I had was determination and, at that time, it was enough for me. I'll never forget the feeling of flying into Manhattan that day and realizing that I was really going to live here. Ready or not.. it was happening.

I started over and moved into an apartment I had never seen, that was double my Portland rent, with a roommate I had never met before, just hoping for the best. There were so many things that could have gone wrong, but luckily, it all worked out. Our first weekend in NYC we jumped right into city living and went to Fashion's Night Out where I had my first experience of getting lost -- you know typical Anna. I walked around downtown for almost two hours trying to find my roommate, confused about how to catch a cab and wishing I had a smartphone I could get directions on. Even though I was lost and getting eaten alive by mosquitos (which is a whole other story), I couldn't have been happier just taking everything in. Eventually, I did find my roommate and a few friends who were visiting, and we walked up and down the streets of Chelsea like we owned the place. I remember passing Neil Patrick Harris and Joan Rivers and just being overwhelmed in the best possible way. That night was just the beginning and I couldn't wait to embrace everything the city had to offer.

After living here for about a month, I met someone who I would go on to spend nearly all my time in the city with. He was calm, cool and collected and was along for the ride of my adventures. We spent our free time checking out the latest and greatest restaurants we had heard about and he got used to waiting to take his first bite until I took pictures for my blog. We spent more weekends and holidays on Long Island than I could count with some of the sweetest people who I'll always consider family. We looked forward to afternoons spent at Central Park and even more so, the big smile that would be on Scooter's face when we walked him out there. Which it should be mentioned, I was always the actual third wheel in that relationship.

I can honestly say I watched more sports during our relationship than the first 21 years of my life combined, but I always looked forward to going to Yankees games aka Garlic Cheesies season. He taught me that NY pizza should be folded when you eat it and, what he would say, the proper pronunciation of Mario -- although that one is still up for debate. It's hard to find a page in my New York story that he wasn't apart of and he was my hardest goodbye. He was my rock and taught me that relationships didn't have to be hard and what it really meant to be life partners. It's not an easy thing to decide you want different things in life after being together so long, but sometimes the best thing you can do for someone you care about is to let them go. 

Beyond love, I met more amazing friends than I could have ever imagined. Year after year I built relationships with some of the kindest and most ambitious people who really got me. People from all over the country and walks of life who also decided to give New York a shot. We'd meet up for brunch, hang out in the park, go out for wine, and girls' nights were always some of my favorite memories. We took in all of the city had to offer, celebrated our wins, hugged it out during the tough times and gave each other a kick in the butt when we needed a boost. You guys held me together when I needed it the most and were my biggest cheerleaders every step of the way. NYC didn't always feel like home to me, but it was my family and friends that really kept me past year 1 and I hope each and every one of you know how much you mean to me. And while I know these will be lifetime relationships (I'm not that easy to get rid of!) not being a subway ride away from all of you is going to be really tough.

Not only was New York a big part of my life personally, but it was huge professionally. I can say for certain it was one of the best decisions I could have made. This city tested me in so many ways and opened the doors to opportunities I would never have had otherwise. It lit up my passion for writing when I started this blog, helped me work my way up in my career and later inspired me to have the courage to start my own business -- something I would have never thought I'd do. There's something about this city that changes you, builds your character and pushes you further than you ever thought you could go and for that, I'll be forever grateful. 

New York is definitely something special and even though I'm ready to go, I'm sure going to miss this crazy place for so many reasons. I'll close things out with a quote from the first blog post I ever published, “Too positive to be doubtful, too optimistic to be fearful, and too determined to be defeated.” It's one of my favorites to this day and one that I think summarizes how I viewed my time here, as well as my next adventure. Goodbyes have always been tough for me, but this one has truly taken everything I have to get through. To closing one chapter and writing another, goodbye NYC.

New York, This is Goodbye
Anna Osgoodby Life + Design :: New York, This is Goodbye

So, BIG news over on the blog today. It's with a lot of excitement/tears/let's be real... alllll of the feels that I announce I've decided to say farewell to NYC. It's been a really tough decision and one I've gone back and forth in my head for years on. After almost 7 years in the city and 10 years living out of state though, it's time to get back to my roots.

Personally, I think what's even scarier than making a decision is actually living through the pain and heartache of the process. It's often not the decision that holds us back, ultimately we know what we want, but actually living through the process to make that decision a reality that is so tough. Especially when others are involved. I hate hurting or disappointing others and this one is a double whammy on all accounts.

Year after year, I tried, and semi-successfully, convinced myself that I could be 100% happy in NYC. And I really thought I could be. After all, I'd built an awesome life, had the most amazing people in my life, and things had really lined up the way I wanted. Especially after I started my own business and was able to go coast-to-coast more. Instead of feeling content with the back and forth though, I just found myself yearning for more time. Those what ifs and thoughts of future regret will crush you though, and sometimes you just can't convince your head and your heart that you want the same thing.

I will forever be thankful for all of my time in the city and this will always be a chapter I'll look back on fondly. I've taken risks. I've loved. I've grown. I've met some of my absolute favorite people. I've both lost and found myself. This city has shaped the person I've become so much and it's going to be really tough to say goodbye.

So what's next? A hot date with a lot of moving details and 2,800 miles to think about if I made the right decision. Truthfully though, while I'm both sad and nervous, I am also really excited for the future. I'm excited to keep expanding my business at Bold & Pop, I'm excited for new adventures (and a lot more outdoors!), I'm excited to drive again, I'm excited to reconnect with some of my best friends, and most of all I'm excited to be a few minutes vs a 6-hour flight home from family. 

Washington, I'm coming home for keeps.