10 Top Things To Do in Ashland, Oregon

10 Top Things To Do in Ashland, Oregon

Beth Glosner  | 

Welcome to Ashland, Oregon—a gem tucked into the Pacific Northwest that offers a delightful blend of art, nature, and cozy small-town charm. Whether you’re here for the Oregon Shakespeare Festival, dropping your kid off at Southern Oregon University, or just passing through on an adventure, you’re in for a treat. With so much to do, where do you start? Don’t worry—I’ve got you covered!

Let’s dig into the 10 top things to do in Ashland so you can make the most of your visit.

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

  1. Emigrant Lake Recreation Area: Ashland’s Outdoor Escape

Just a short drive from downtown Ashland, Emigrant Lake is perfect for nature lovers and outdoor enthusiasts. Whether you’re looking for a scenic picnic spot, a place to launch your boat, or even a fun day with the kids on the water slides (yes, they have slides!), Emigrant Lake has it all.

Pro tip: If you’re an early bird, you might even catch a glimpse of local wildlife. Hawks, deer, and even the occasional crane love to make an appearance. And, if you’re lucky, you might witness the high school or university crew teams practicing on the water. Be sure to bring a camera to capture the stunning views of the lake and surrounding hills—ideal for your Instagram story!

 Emigrant Lake—where nature meets tranquility. 

  1. Oak Knoll Golf Course: Swing Away

Ashland’s only golf course, Oak Knoll, offers nine holes of challenging fun. Whether you’re an experienced golfer or just getting started, Oak Knoll has something for everyone, including golf lessons for kids and adults.

They’ve also got Pickleball and FootGolf (yes, FootGolf!), so if you’re feeling adventurous, you can try something a bit different.

Pro tip: Oak Knoll is also a great place to hang out with friends, whether you’re playing a round or enjoying their clubhouse for a private BBQ.

Swinging into fun at Oak Knoll Golf Course—Ashland’s perfect spot for a round of golf

  1. Rogue Valley Symphony: Music That Moves You

If you love classical music, the Rogue Valley Symphony is a must-see. They perform throughout the Rogue Valley, including Ashland, Medford, and Grants Pass, with concerts happening from September through April.

A night at the symphony is the perfect way to add a little culture to your Ashland trip. Dress up, grab your tickets, and let the music sweep you off your feet.

A night at the Symphony—Ashland’s hidden gem for music lovers.

  1. Southern Oregon University: Campus Charm

You don’t have to enroll in classes to appreciate the beauty of Southern Oregon University (SOU). This campus is home to some unique architecture, stunning views, and local wildlife—don’t be surprised if you see deer lounging around on the grass.

Take a stroll through the Schneider Museum of Art, located right on campus. With rotating contemporary art exhibits, you’ll find bold, creative displays from both local and international artists. Free guided tours on Tuesdays will give you more insight into the art and artists on display.

The Oregon Center for the Arts at Southern Oregon University is a vibrant hub for creativity, offering a diverse schedule of artistic events throughout the year. From captivating theater performances and soul-stirring concerts to thought-provoking art exhibits, the center brings the best of the arts to campus. Whether you’re a seasoned enthusiast or just looking to explore something new, the Oregon Center for the Arts invites you to immerse yourself in a dynamic world of talent and inspiration. Keep an eye on their calendar—you won’t want to miss what’s coming next!

Pro tip: Swing by the Hannon Library for some peaceful vibes. The surrounding gardens are perfect for a quiet walk, and the deer think so too—just don’t feed them!

 Art, nature, and quiet study spots—SOU has it all. 

  1. Ashland Independent Film Festival: Lights, Camera, Action!

The Ashland Independent Film Festival (AIFF) is a major event, drawing movie buffs from around the country. Hosted in April and October, the festival showcases the best in independent cinema at the Varsity Theatre—a vintage venue that only adds to the charm.

Even when the festival isn’t in full swing, AIFF is active in the community, collaborating with local museums like ScienceWorks to teach filmmaking to kids and hosting year-round events. It’s a must-visit if you’re into indie films or just looking for something offbeat.

Catching a flick at the Ashland Independent Film Festival 

  1. First Fridays and Ashland Art Works: Art Lover’s Paradise

Ashland is an art lover’s dream, and Ashland Art Works is one of the best spots to see local creativity in action. This artist collective features everything from sculpture and pottery to jewelry and paintings.

But if you really want to dive into the local art scene, make sure you’re here for First Fridays. On the first Friday of every month, Ashland’s galleries and shops stay open late, hosting receptions, art demonstrations, and, yes, sometimes free wine! It’s the perfect way to experience the town’s artistic side.

Pro tip: Don’t forget to stop by Ashland Art Works during your First Friday art stroll—you never know what hidden gem you’ll find to take home.

Exploring Ashland’s vibrant art scene at First Friday 

  1. Oregon Cabaret Theatre: Dinner and a Show

For a memorable night out, head to the Oregon Cabaret Theatre for dinner and a show. Housed in a former 1911 Baptist Church, the Cabaret is the perfect spot for entertainment in a cozy, intimate setting. They offer a delicious dinner with the show, and their desserts are worth every bite!

From musicals to plays, the performances here are top-notch, making it a staple of Ashland’s arts scene.

Dinner and a show? Yes, please!

  1. Lithia Park: 100 Acres of Pure Beauty

Nestled right in downtown Ashland, Lithia Park is a natural gem. Whether you want to go for a leisurely stroll, have a picnic, or explore hiking trails, Lithia Park has you covered. The park is huge, spanning 100 acres, with something new to discover around every corner.

From duck ponds and fountains to the beautiful Japanese-style garden, Lithia Park is perfect for unwinding and soaking in nature.

If you’re in the mood for something a bit more challenging, check out the Lithia Park Hillside Trail—a five-mile hike with breathtaking views. Be prepared for a bit of a climb, but it’s well worth the effort!

 Nature at its finest in the heart of Ashland 

  1. Oregon Shakespeare Festival: A Must-See

If there’s one thing Ashland is known for, it’s the Oregon Shakespeare Festival (OSF). This world-renowned festival runs from February to October, offering everything from classic Shakespearean plays to contemporary works.

OSF’s three theaters, including the iconic outdoor Allen Elizabethan Theatre, are an experience in themselves. Whether you’re catching a matinee or an evening performance, the festival is a can’t-miss Ashland experience.

Pro tip: Don’t forget to catch the Green Show—a free outdoor performance before the main event during the summer months!

Experience the magic of Ashland’s Green Show—free outdoor performances that bring the Oregon Shakespeare Festival to life!

  1. Oregon Chocolate Festival: A Sweet Escape

Looking for a delicious reason to visit Ashland? The Oregon Chocolate Festival is a must-see for chocoholics and adventure seekers alike. Mark your calendars in March for this yearly event, and prepare for a weekend filled with chocolate creations crafted by artisan makers from across the West Coast.

Start the weekend with a decadent Chocolate Maker’s Wine Dinner, dive into educational presentations and demos, and don’t forget to treat yourself to the delightful Chocolate Brunch on Sunday. 

Pro tip: Turn your visit into a chocolate-filled getaway by booking the Chocolate Escape Package at the Ashland Hills Hotel & Suites—the festival’s venue. Or, for a touch of luxury, opt for the Chocolate Dreams Package at the historic Ashland Springs Hotel, right in the heart of downtown Ashland.

Sweet indulgence at the Oregon Chocolate Festival—where every bite is an adventure.

Ashland Awaits!

Ashland is a hidden gem that offers far more than you might expect. From outdoor adventures at Emigrant Lake to world-class performances at the Oregon Shakespeare Festival, there’s something for everyone in this charming town. If you’re looking for the perfect place to rest during your visit, be sure to check out my blog, Where to Stay in Ashland: Your Ultimate Cozy Corner, for some great recommendations.

Whether you’re here for a weekend getaway or an extended stay, these top experiences are a must-do and will make your time in Ashland truly unforgettable!

Stay curious, stay hungry, and keep exploring!

-Beth

The Perfect Length for Your First Solo Trip: How Long Should You Go?

Beth Glosner  | 

If you’re considering your first solo trip, congratulations! You’re in for an adventure that will be equally thrilling and transformative. But there’s one big question that every new traveler has: How long should my first solo trip be?

The answer isn’t one-size-fits-all, but I’m here to help guide you through making that decision. Solo travel can seem daunting at first (we’ve all been there!). But a trip of the right length will give you time to adapt, explore, and enjoy it.

So, grab your favorite cozy blanket and a cup of coffee. We’re about to dig into everything you need to know to plan the perfect solo adventure. Let’s Dig In.

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

How long should my first solo trip be?

Let’s get straight to it: your first independent trip should last about one to two weeks. Why? It lets you adjust, build confidence, and find your travel rhythm.

Here’s the breakdown:

  • Week 1: You’ll spend the first few days finding your footing. Independent travel has a learning curve. You must trust your gut, navigate a new place, and deal with first-day jitters. But, by week’s end, you’ll feel more confident. You’ll think on your feet and make the most of your time.
  • Week 2: This is where the magic happens. You’ll start to enjoy your trip. You’ll explore its culture, food, and experiences. No need to figure things out. By this point, you’ll feel more like a local than a wide-eyed tourist.

Now, I know what you’re thinking: “Two weeks? That’s a lot of time!” But hear me out. It’s enough time to ease into solo travel without rushing. It also prevents burnout from being on your own for too long. Plus, having a few extra days can come in handy for spontaneous adventures (and we all know those are the best kind!).

But, what if I can’t do two weeks?

No worries! If two weeks feels like too much, consider starting with a 7-day trip. A week is a good time to ease into solo travel. It’s especially true if you’re going somewhere easy to navigate or not far from home. For first-time independent travelers, I’d recommend New York City, Austin, or Portland. If you’re in the U.S., they’re familiar, have much to do, and have reliable transport. If you’re in another country, find a large city nearby or another location in your country.  Bonus: You’ll have plenty of time to unwind and explore without feeling overwhelmed.

Just make sure your destination aligns with your comfort level. Some places suit solo travelers better than others. This can affect your comfort on your trip.

How to Maximize a 7-Day Solo Adventure

If you’re going on a one-week trip, here’s how to make the most of it:

  1. Keep It Simple: Choose one key city or region to explore. You don’t want to spend your whole trip in transit. So, aim for places with enough activities to fill your days. But, not so many that you’ll be running from one thing to the next.
  2. Plan for Downtime: Solo travel is exhilarating, but it can be exhausting if you’re always on the move. Schedule some time for yourself. It could be a coffee at a local café or relaxing in your hotel or Airbnb.
  3. Stay Flexible: The best part of independet travel is the freedom to be spontaneous. Don’t feel like you need to plan every minute. Leave room for surprises. You might find a hidden bookstore or a charming local market!
  4. Connect with other solo female travelers through the FB page Solo Female Travelers (FIRST FB group for women who travel solo!). They can help you with itinerary ideas or share your travel wins and challenges.

Pros and Cons of a Longer Trip (Two Weeks or More)

If you’ve got the time and flexibility, a two-week trip might be exactly what you need. Here’s what to expect from a longer solo journey:

Pros:

  • Deeper immersion: You can deeply embrace the destination’s culture, cuisine, and vibe.
  • Less stress: More time means less pressure to cram everything into a few days. You can go at your own pace.
  • Personal growth: The more time you spend alone, the more you’ll get comfortable with being self-reliant. That skill will stick with you long after your trip.

Cons:

  • Homesickness: After a few days, some solo travelers miss familiar faces and routines. Schedule regular calls or video chats with friends and family to stay connected. This will help combat it.
  • Stressful: You are the sole person making the directions without someone to fall back on. Traveling to a new country with a language barrier, new food, and people can be daunting and stressful. A good cry is bound to happen. This is completely normal and healthy.
  • Lonely: Don’t get me wrong I love solo travel but it can be lonely at times. The desire to share an experience with someone. During our travels connect with others and share your travel stories.
  • Budget: Longer trips can result in significant expenses. Plan your budget carefully. Account for accommodation, food, and activities.

5 Tips for Making the Most of Your First Solo Trip

  1. Start Small: For your first independent adventure, pick a destination that feels manageable. A town or city where people speak your native language and have good public transportation.
  2. Choose Safe Accommodations: Look for accommodations with great reviews. Hostels, B&Bs, or small boutique hotels offer opportunities to meet other travelers. All the while still giving you personal space.
  3. Learn Basic Phrases: If you’re going to a non-English-speaking country, learn some key phrases in the local language. They can help. (Plus, it’s fun to surprise locals with your efforts!)
  4. Trust Your Gut: If something feels off, trust your instincts. Whether it’s a sketchy situation or simply a tour you’re not vibing with, it’s okay to walk away. Your safety is always first.
  5. Document Your Journey: Keep a journal, take photos, or start a travel blog. Not only will this help you reflect on your trip, but it also gives you something to look back on with pride.

 Taking a solo coffee break and soaking in the vibes!

How to Know You’re Ready for a Solo Trip

Still wondering if you’re truly ready for your first solo trip? Here are a few signs that you’re up for the challenge:

  • You’re comfortable doing things alone, like eating out or going to a movie.
  • You’ve planned a trip before, even if it was with others.
  • You’re ready to step out of your comfort zone and embrace the unknown.

If these sound like you, then get ready to book that flight!

How Long Should Your First Solo Trip Be?

Ultimately, the length of your trip depends on your comfort, destination, and personal preferences. For most people, 1-2 weeks is the sweet spot for a first independent adventure. It gives you time to adjust, explore, and return home feeling empowered by your experience.

Ready to take the plunge? Start planning your self-guided adventure today. Whether it’s a quick getaway or a longer journey, embrace every moment! And don’t forget to check out my guide to the 7 best travel apps for independent female travelers to help make your trip even smoother.

Stay curious, stay hungry, and keep exploring!

 -Beth

Top 7 Must-Have Travel Apps for Female Adventurers | Stay Safe & Organized

Beth Glosner  | 

Let’s Dig In!

Solo travel is one of the most empowering experiences you can have. You get to explore new places at your own pace, dive deep into local culture, and discover new things about yourself along the way. But let’s be real, it’s not all sunshine and scenic routes. Sometimes, you need a little extra help navigating unfamiliar streets or ensuring your safety. That’s where travel apps come in! Whether you need help staying organized, finding Wi-Fi, or ensuring your safety, these apps are here to make solo travel as smooth as possible.

In this post, I’ll break down the best solo travel apps every female adventurer should have on her phone. With these trusty tools by your side, you’ll be exploring with confidence in no time!

Disclaimer

This post contains affiliate links to the products that I use and trust. This means that I might receive a small commission (at no extra cost to you) if you make a purchase using any of my links below. See full disclosure here

  1. Google Maps: The Modern-Day Compass

Google Maps has your back, whether you’re strolling through the hustle and bustle of Manhattan or wandering Central Park. The app gives you real-time directions for every possible mode of transport—walking, biking, public transit, you name it. And the best part? It works offline! Yep, download your maps in advance and say goodbye to pricey international data charges or getting lost in the city that never sleeps.

Real-world example: During my solo trip to New York, I downloaded the entire Manhattan map before heading out for a day of exploring. And yes, I have been lost in Central Park before! But with the offline map, I quickly found my way back to a scenic spot without missing a beat.

 Navigating Manhattan with ease—Google Maps to the rescue!

  1. TripIt: Your Personal Travel Assistant

No one needs 43 confirmation emails cluttering their inbox.

TripIt is your one-stop shop for organizing travel plans. Instead of searching through your inbox for flight details or hotel reservations, simply forward your confirmation emails to TripIt, and it’ll create a neat, organized itinerary for you. The app even works offline, so you can access your travel plans without Wi-Fi.

Pro Tip: Share your TripIt itinerary with family or friends. That way, even when you’re off the grid, your loved ones will know exactly where you are.

No more email hunting! All my travel details in one place thanks to TripIt.

  1. bSafe: Safety First, Always

Because adventure is fun, but safety is a must.

Whether you’re exploring city streets or hiking in the wilderness, bSafe ensures you’re never truly alone. It allows you to share your location with trusted contacts and has an SOS button that notifies them in case of emergencies. What’s even cooler? You can activate the app hands-free using voice commands.

True Story: While hiking in Oregon, I used bSafe’s “Follow Me” feature, which kept my friend updated on my location in real time. There were no emergencies, but having that peace of mind made the hike much more enjoyable.

Exploring solo but never alone with bSafe watching my back.

  1. PackPoint: Because Overpacking is So 2010

Pack smarter, not harder.

If you’re like me and pack way more than you need “just in case,” PackPoint is about to be your new best friend. The app helps you create a custom packing list based on your destination, the weather, and planned activities. Going to a beach town? Pack your swimsuit. Headed for a hiking trip? Don’t forget that rain jacket.

Fun Fact: PackPoint adjusts your packing list depending on the weather forecast for your destination. You’ll never be caught unprepared!


Travel light and smart! Thanks, PackPoint, for keeping me on track.

  1. WiFi Map: Stay Connected Without Breaking the Bank

No more overpriced coffee just for Wi-Fi.

WiFi Map helps you find free Wi-Fi spots all around the world. Whether you’re in a bustling city or a remote village, this app will point you to the nearest available Wi-Fi. Plus, you can download Wi-Fi locations ahead of time, making it super easy to stay connected when traveling.

Pro Tip: Use the app to scout out cool cafés with free Wi-Fi. You’ll find yourself sipping coffee in the best local spots while staying connected with friends or planning your next adventure.

Wi-Fi and a latte, anyone? Staying connected while exploring Paris with WiFi Map.

  1. Meetup: Solo Doesn’t Mean Lonely

Because solo travel doesn’t mean being alone.

Meetup is the perfect app for when you want to socialize during your travels. It connects you with locals or fellow travelers who share your interests. Whether you’re looking for a hiking group, a language exchange, or even a cooking class, you’ll find something fun on Meetup.

True Story: On a solo trip to Portland, Oregon, I decided to join a walking tour that explored the city’s best food spots. Not only did I get to taste some delicious local treats, but I also struck up a conversation with a fellow traveler from Colorado. We’ve kept in touch and even swapped travel tips for future adventures!


Joined a Meetup for a Portland walking tour 

  1. XE Currency: For When Math Isn’t Your Thing

Real-time currency conversions at your fingertips.

If you’ve ever struggled to mentally convert foreign currency while shopping at a street market, XE Currency will be your new go-to. The app offers real-time exchange rates and works offline, making it ideal for when you’re in areas without service.

Pro Tip: Bookmark your commonly used currencies for quick conversions while on the go.


Never overpay for that handmade scarf again—XE Currency has your back.

Solo Travel Just Got Easier!

With these seven apps in your travel toolkit, solo female travel is a breeze. From staying safe with bSafe to organizing your itinerary with TripIt and finding free Wi-Fi with WiFi Map, you’ll be exploring with confidence and ease. And while you’re at it, don’t forget to indulge in local flavors—check out my post on Culinary Travel: Explore the World Through Food or more delicious tips. So go ahead—download these essentials, pack your bags, and embark on the adventure of a lifetime. You’ve got this!

Stay curious, stay hungry, and keep exploring!

-Beth