The Ultimate Medford Oregon Weekend Adventure Itinerary

Medford, Oregon is a mid-size town in Southern Oregon that you may not have heard of. We fit so much into our Medford, Oregon weekend itinerary, but we barely scratched the surface of how many things to do in Medford there are! It wasn’t long ago that it popped up on our radar as we were building our Crater Lake National Park itinerary.

We initially thought it was a place we could stay when visiting the national park, but we soon realized Medford is the perfect basecamp for so many epic adventures. It’s known as the Heart of the Rogue Valley and we had the best weekend trip in Medford!

Medford is perfect for a weekend getaway due to the variety of activities and outdoor adventures you can find there. We worked with Travel Medford to build the ultimate Medford, Oregon weekend itinerary!

Where to stay in Medford

We stayed at the brand new Compass Hotel by Margaritaville. Not only was it very close to downtown Medford, but we loved the contrast of the palm trees and margaritas by the pool, and the lush forests of the Pacific Northwest. 

The hotel has a complimentary breakfast buffet each morning which we enjoyed by the pool as well as an on site restaurant: 5 o’Clock Somewhere Bar and Grill. 

How to get to Medford

If you are not within driving distance, the easiest way is to fly into the Rogue Valley International Medford Airport (MFR). There are several popular rental car locations within the airport terminal, so you’ll be on your way in no time. The airport has flights all day into the late evening which is perfect in case you are flying from the east coast. It’s a short drive from downtown and all the local hotels.

It was so easy to get our car from Avis because the rental agencies are in terminal! Rental car agencies located in the terminal:

• Avis
• Alamo
• Budget
• Enterprise
• National

The drive is not bad from most of the points in Oregon, so if you’ll already be in the area, you can get to Medford in:

• Portland: 4 hour drive
• Bend: 2.5 hour drive
• Eugene: 2.5 hour drive

Medford Itinerary

We had 3 full days in the area for our Medford, Oregon weekend itinerary since we arrived in Medford late Thursday night, and left late Sunday.

Day 1

Our day started at Forage Coffee which is a beautiful plant shop and cafe that serves amazing coffee and light breakfast items. They served up some of the best oat milk lattes and avocado toast. We loved the decor here and we think it might be the best coffee shop in Medford!

After getting our caffeine fix, we headed to Prescott Park to explore. There are a variety of trails at Prescott Park, and Roxy Ann Peak is the jewel of the park with the best panoramic views in Medford. This is where we first saw how expansive the Rogue Valley really is.

We headed back to our hotel for lunch at 5 o’Clock Somewhere Bar and Grill where we had margaritas and grain bowls. Afterward, we relaxed by the pool and soaked up the sun and warm weather.

We were lucky enough to be in town at the same time as the inaugural Heart of the Rogue Festival in downtown Medford! There was tons of local businesses, live music, and delicious vegan cupcakes. We also had a great dinner at the Common Block Brewing Company before heading to bed for an early wake up call.

Day 2

Since we are a bit crazy and love to see the sun rise, we woke up and left Medford at 5 AM and drove two hours north to Crater Lake National Park. If you are crazy like us, we highly recommend adding sunrise at Crater Lake to your Medford, Oregon weekend itinerary! We recommend that you pack some breakfast and lunch, because there are not many food options especially during the winter months.

Fun fact: Crater Lake, which formed from the collapse of a Volcano, is the deepest lake in the US and the 9th deepest lake in the world!

We watched the sunrise from Watchman Overlook. You can also take the Watchman Peak trail up to the watchtower for a higher view of the lake.

After sunrise, we drove the Rim drive clockwise. This 33 mile drive takes you along the rim of the lake with several pullouts and hiking options. Since we spent a lot of time photographing the rim, we didn’t have time to do the hikes along the way. It took us about two hours to do the whole drive, stopping for photos at almost every viewpoint.

After making the full circle, we broke off when we got back to Watchman Overlook to head further north to see some waterfalls! Within a short drive we saw Whitehorse Falls, Watson Falls and ended at Toketee Falls. You can travel to the base of Toketee Falls, but only if you are in great physical shape, have excellent traction hiking boots, and the ground is dry.

On the way back to Medford, we stopped at Mill Creek Falls, Natural Bridge Overlook, and the Rogue River Viewpoint.

After an epic day of adventures, we relaxed by the hotel fire pit and ate some fish tacos and beer.

Day 3

We woke up on our last day in Medford, this time after the sun had already risen, to a cool and bright morning! We enjoyed the breakfast buffet at Compass Hotel by the pool while we listened to Jimmy Buffett escape to the island we felt we were on. 

If you’ve been following us for a while, you might know that we love wine. From Palisade, Colorado to Stellenbosch, South Africa, we always end up in a tasting room when we are visiting wine country. 

We started out at 2Hawk Vineyard and Winery which had our favorite wine of the day. The parking lot is directly in front of rows of vines which had delicious looking grapes hanging from them. They had a great patio and lawn area to enjoy our tasting.

Next, we stopped at Dancin Vineyards which you could guess by the name of it was surrounded by vines. Right near the tasting area is a beautiful garden with a Koi pond in the middle.

Finally, we ended up at Relik Winery for our last tasting and lunch. Yes, we stopped here because they have Alpacas and Donkeys. We enjoyed a glass of wine and artisan pizza in the middle of some fruit trees on their lawn.

There are 33 wineries in the Rogue Valley and we wish we could have tried them all, but alas, we will be back!

Please remember to leave no trace and keep Medford beautiful!