New Chat

Download App

Ask me about your trip!

There are no messages for this conversation.

Roam Around

5-day trip to Ashland, Oregon

5-day trip to Ashland, Oregon Itinerary

Last updated: 2024 Jun 14

Exploring Ashland

Morning
Start your day with a delicious breakfast at Greenleaf Restaurant. Afterward, embark on the Medford Private City Scavenger Hunt in Medford, just a short drive away. Spend the morning exploring the city and solving clues to uncover hidden gems.
Afternoon
Head back to Ashland for lunch at Standing Stone Brewing Company, where you can enjoy craft beers and a diverse menu. In the afternoon, visit the Oregon Shakespeare Festival and immerse yourself in world-class theater performances.
Evening
For dinner, indulge in Italian cuisine at Pasta Piatti. Afterward, take a leisurely stroll through Lithia Park and enjoy the beautiful scenery.
Bedtime
Find amazing hotels in Ashland, Oregon.
Visit Medford Private City Scavenger Hunt in Ashland, Oregon

Medford Private City Scavenger Hunt

Book Now
Visit Aoraki/Mt. Cook National Park in Ashland, Oregon
star4.73

Oregon Shakespeare Festival

Book Now

Outdoor Adventures

Morning
Start your day with a hearty breakfast at Ruby's. Then, venture out to Mount Ashland for a scenic hike and breathtaking views of the surrounding area. Spend the morning exploring the trails and enjoying the fresh mountain air.
Afternoon
After your hike, grab a quick snack at Agave and head to Emigrant Lake for some water activities. Rent a kayak or paddleboard and spend the afternoon on the lake, enjoying the sunshine and tranquility.
Evening
For dinner, treat yourself to a seafood feast at Omar's Fresh Seafood & Steaks. Afterward, unwind at Louie's Restaurant with a cocktail or glass of wine.
Bedtime
Find amazing hotels in Ashland, Oregon.

Culinary Delights

Morning
Start your day with a delicious breakfast at Kobe Restaurant. Then, explore the local farmers' market and indulge in fresh produce and artisanal goods.
Afternoon
For lunch, head to Thai Pepper and savor authentic Thai cuisine. In the afternoon, visit the Schneider Museum of Art and admire contemporary artworks by local and international artists.
Evening
Enjoy a fine dining experience at Martolli's, known for its gourmet pizzas and Italian dishes. After dinner, check out Dragonfly, a trendy bar with craft cocktails and live music.
Bedtime
Find amazing hotels in Ashland, Oregon.

Cultural Immersion

Morning
Start your day with a cup of coffee at Hiroshi, a local favorite. Then, visit the ScienceWorks Hands-On Museum and engage in interactive exhibits and educational activities.
Afternoon
For lunch, head to Amuse and enjoy a fusion of Mediterranean and Northwest flavors. In the afternoon, explore the Southern Oregon University campus and visit the Schneider Museum of Art if you haven't already.
Evening
Indulge in a farm-to-table dining experience at Larks Home Kitchen Cuisine, known for its locally sourced ingredients and innovative dishes. Afterward, relax at Callahan's Lodge with a drink and enjoy the panoramic views of the surrounding mountains.
Bedtime
Find amazing hotels in Ashland, Oregon.
Visit Brunswick Monument in Ashland, Oregon
star4.49

ScienceWorks Hands-On Museum

Book Now
Visit Penthes Estate (Le Domaine du Château de Penthes) in Ashland, Oregon

Southern Oregon University

Book Now

Food and Shopping

Morning
Start your day with breakfast at Brothers' Restaurant, a local institution known for its hearty meals. Then, explore the unique shops and boutiques in downtown Ashland, such as Café 116 and Pangea.
Afternoon
For lunch, try the delicious Brazilian cuisine at Beija Flor. Afterward, visit the Ashland Art Center and browse through the galleries showcasing the works of local artists.
Evening
Enjoy a memorable dinner at The Peerless Restaurant & Bar, known for its upscale ambiance and gourmet cuisine. End your trip with a visit to Taroko, a stylish lounge with creative cocktails and a vibrant atmosphere.
Bedtime
Find amazing hotels in Ashland, Oregon.
Visit Padangbai (Padang Bai) in Ashland, Oregon
star4.90

Café 116

Book Now
Visit Cave Temple (Wat Suwan Kuha) in Ashland, Oregon
star3.73

Pangea

Book Now
kayakFind the right stay during your trip.
Got a question about your trip?