Ashland, Oregon - 5 Days Itinerary

Arrive & Check-in

Arrive in Ashland and check into your spacious vacation rental, allowing time to settle in and unwind after your drive from Idaho.

Confirm check-in procedures and access details for your rental prior to arrival.

Leisurely Lithia Park Walk

Enjoy a gentle walk through the scenic Lithia Park, a beautiful urban park with walking trails, duck ponds, and charming scenery.

It's a perfect way to stretch your legs and get acquainted with Ashland's natural beauty.

Wear comfortable shoes. The lower parts of the park are relatively flat and easy to navigate. Restrooms are available.

Welcome Dinner

Enjoy a welcome dinner at a highly-rated local restaurant.

Ashland offers various dining options from casual to fine dining, many with menus featuring local ingredients.

Reservations are highly recommended for a group of 8, especially during peak season or for specific restaurants.

Oregon Shakespeare Festival Exploration

Visit the grounds of the renowned Oregon Shakespeare Festival.

Depending on the schedule, you might enjoy a backstage tour (seasonal) or explore the gift shop and exhibit areas. A gentle way to experience Ashland's cultural heart.

Check their website for tour availability and any matinee performances during your visit. The main season typically starts in late February/early March.

Downtown Lunch & Shops

Enjoy lunch at a charming cafe or bistro in downtown Ashland, followed by some time to browse the unique boutiques and art galleries.

Many independent shops and galleries offer local crafts and art. Support local businesses!

Belle Fiore Estate & Winery

Experience a tasting at Belle Fiore Estate & Winery, known for its beautiful grounds and European-inspired architecture.

Enjoy their wines in a serene setting.

Consider making a reservation for a tasting, especially for a group of 8. Enjoy the scenic views.

Dinner & Relaxed Evening

Dine at another excellent Ashland restaurant or opt for a relaxed evening cooking at your vacation rental, enjoying each other's company.

If dining out, consider restaurants offering diverse menus to cater to different tastes. Many offer early bird specials.

Escape Ashland Challenge

Engage in a fun and interactive group challenge at Escape Ashland.

They offer unique live-action escape rooms perfect for teamwork and laughter.

Book your escape room experience in advance to secure your preferred time slot and room. They have multiple rooms, some themed around 'The Scottish Play'.

Visit Ashland Library

Enjoy a quiet visit to the Ashland Library, a beautiful community hub.

It's a nice opportunity for a relaxed browse or to appreciate its architecture.

Check for any local art exhibits or community events that might be happening during your visit.

Lunch in Downtown

Savor another delightful lunch at one of Ashland's diverse eateries.

Explore options ranging from casual cafes to restaurants offering fresh, local cuisine.

Many restaurants offer outdoor seating which can be lovely in April, weather permitting.

Oregon Cabaret Theatre Matinee (Optional)

If available, consider attending a matinee performance at the Oregon Cabaret Theatre.

They offer first-class entertainment and a unique venue. Alternatively, enjoy some free time or another gentle walk.

Check their schedule in advance for matinee options for your dates. Booking tickets ahead of time is essential for shows.

Friday Evening Dinner

Enjoy dinner, perhaps trying a different culinary style or revisiting a favorite spot from the past few days.

Ashland's culinary scene is vibrant, offering many options from Italian to farm-to-table. Consider what cuisine the group is in the mood for.

Leisurely Breakfast

Enjoy a relaxed breakfast at your vacation rental, preparing for a day of scenic beauty and local flavors.

Utilize the rental's kitchen for a homemade meal or pick up pastries from a local bakery.

Belle Fiore Estate & Winery

Experience wine tasting amidst the beautiful Tuscan-inspired estate and gardens.

Enjoy their award-winning wines.

Consider booking a tasting in advance for a group. They offer a range of varietals and a stunning setting.

Lunch in Downtown Ashland

Savor a delightful lunch at one of Ashland's charming downtown restaurants, offering various cuisines to suit all tastes.

Options range from casual cafes to more upscale dining. Reservations recommended for larger groups.

Resistance Wine Company

Enjoy a more intimate wine tasting experience at this highly-rated local wine bar and store.

A great spot to discover unique local wines.

This spot is often praised for its friendly atmosphere and knowledgeable staff. Perfect for continuing your wine exploration.

Oregon Cabaret Theatre

Enjoy an evening of first-class entertainment and dining.

Check their schedule for performances during your visit.

The theatre offers dinner and a show experience. Book tickets well in advance, especially for a group of 8. The schedule for April will typically be available months prior.

Leisurely Brunch

Enjoy a final, relaxed brunch at your vacation rental or a local cafe before your day of exploration and departure preparations.

Consider a spot like Morning Glory Restaurant or Brother's Restaurant for a classic Ashland brunch.

Stroll Through Lithia Park

Enjoy a gentle walk through the beautiful Lithia Park, exploring its tranquil ponds, Japanese garden, and natural trails.

A perfect way to enjoy Ashland's natural beauty at a leisurely pace. Paths are generally flat and accessible. April should offer beautiful spring blooms.

Ashland Library Visit

For those interested in a quiet cultural stop, the Ashland Library offers a beautiful space and often features local art or historical exhibits.

A peaceful option, especially if weather is inclement or for a moment of quiet reflection before departure.

Farewell Lunch

Enjoy a casual farewell lunch at a local eatery, reflecting on your wonderful trip to Ashland.

Choose a spot near your rental or on your route out of town for convenience.

Prepare for Departure

Gather your belongings, tidy up the vacation rental, and get ready for your drive back to Idaho.

Ensure all personal items are packed and rental instructions for checkout are followed.