01

Day 01

Washington Park, Pittock Mansion & the Pearl

Gardens in the hills, a mansion with a view and an evening in the Pearl.

1. Morning

   International Rose Test Garden

   Take the MAX to Washington Park and walk to the Rose Test Garden while the light is soft and the terraces are quiet.

2. Late Morning

   Portland Japanese Garden

   Cross the road to the Japanese Garden, with timed tickets booked in advance, and wander its ponds and moss gardens.

3. Lunch

   Northwest 23rd Avenue

   Head down to Northwest 23rd Avenue for lunch at a cafe, then browse its boutiques.

4. Afternoon

   Pittock Mansion

   Visit the mansion and its lawn for the view over the city and Mount Hood.

5. Late Afternoon

   Powell's City of Books

   Get lost in the color-coded rooms of Powell's on West Burnside.

6. Evening

   Pearl District

   Have dinner in the Pearl District, at Andina or another neighborhood favorite.

02

Day 02

Downtown, Old Town & the Waterfront

Portland's living room, a Chinese garden, the river and a famous dinner.

1. Morning

   Pioneer Courthouse Square

   Start in Portland's living room, then walk the South Park Blocks to the Portland Art Museum.

2. Late Morning

   Portland Art Museum

   Explore the collections and the new glass Rothko Pavilion, reopened in November 2025.

3. Lunch

   Food cart pod

   Grab lunch at a downtown food cart pod.

4. Afternoon

   Lan Su Chinese Garden

   Stroll the walled garden and stop for tea in the teahouse.

5. Late Afternoon

   Tom McCall Waterfront Park

   Walk the riverfront loop across the Steel Bridge and back along the Eastbank Esplanade, passing the Keep Portland Weird sign.

6. Evening

   Le Pigeon

   Book dinner at Le Pigeon, or walk next door to Canard for a more casual meal.

03

Day 03

The East Side: Division, Hawthorne & Mount Tabor

Neighborhood streets, a volcano park and Portland's food scene.

1. Morning

   Pine State Biscuits

   Start with a biscuit sandwich, a Portland breakfast classic.

2. Late Morning

   Hawthorne Boulevard

   Browse vintage shops, bookstores and cafes along Hawthorne.

3. Lunch

   Nong's Khao Man Gai

   Try the famous chicken and rice that started as a food cart.

4. Afternoon

   Mount Tabor Park

   Walk to the summit of the volcanic cinder cone and its reservoirs.

5. Late Afternoon

   Division Street

   Explore Division Street's bakeries, bars and shops.

6. Evening

   Kann

   Have dinner at Kann, booked well in advance, or at another east side favorite.

04

Day 04

Columbia River Gorge Day Trip

Waterfalls, viewpoints and the Historic Columbia River Highway.

1. Morning

   Vista House at Crown Point

   Drive east about 30 minutes to the domed viewpoint high above the Columbia River.

2. Late Morning

   Multnomah Falls

   Follow the Historic Columbia River Highway past Latourell Falls to Multnomah Falls, checking summer permit rules, and walk up to the Benson Bridge.

3. Lunch

   Cascade Locks

   Stop for lunch in the small river town of Cascade Locks, near the Bridge of the Gods.

4. Afternoon

   Hood River

   Continue to Hood River for views over the Columbia and the orchards of the valley.

5. Late Afternoon

   Historic Columbia River Highway

   Drive back toward Portland, stopping at a viewpoint or a short waterfall trail.

6. Evening

   Ox

   Return to Portland for a wood-fired dinner at Ox.

05

Day 05

Science, Zoo & Riverside Fun

A science museum, a submarine, a zoo and an evening by the river.

1. Morning

   Oregon Museum of Science and Industry

   Explore the hands-on halls and tour the USS Blueback submarine.

2. Late Morning

   Eastbank Esplanade

   Walk the riverside path and its floating walkway with views of downtown.

3. Lunch

   Food cart pod

   Let everyone choose their own lunch at a food cart pod.

4. Afternoon

   Oregon Zoo

   Take the MAX to Washington Park and spend the afternoon at the zoo.

5. Late Afternoon

   Salt & Straw

   Head to Northwest 23rd Avenue for an ice cream break.

6. Evening

   Voodoo Doughnut

   End the day with a quirky doughnut in Old Town.

06

Day 06

Mount Hood Day Trip

A snowy volcano, a historic lodge and a mountain lake.

1. Morning

   Mount Hood

   Drive about 90 minutes east to Mount Hood, checking road conditions in winter.

2. Late Morning

   Timberline Lodge

   Visit the historic lodge high on the mountain, built in the 1930s.

3. Lunch

   Timberline Lodge

   Have lunch at the lodge with views of the summit.

4. Afternoon

   Trillium Lake

   Walk around the lake for the classic reflection of Mount Hood.

5. Late Afternoon

   Government Camp

   Stop in the mountain village before driving back.

6. Evening

   Matt's BBQ

   Back in Portland, finish with Texas-style barbecue in North Portland.

07

Day 07

Forest Park, St Johns & Mississippi

A forest walk, a Gothic bridge and live music.

1. Morning

   Forest Park

   Walk the Lower Macleay Trail along Balch Creek to the Witch's Castle.

2. Late Morning

   Hoyt Arboretum

   Continue through the arboretum's trails if you have energy, or return to Northwest.

3. Lunch

   Northwest Portland

   Have lunch near Northwest 23rd Avenue.

4. Afternoon

   St Johns Bridge

   Head to Cathedral Park to see the arches of the St Johns Bridge.

5. Late Afternoon

   Alberta Street

   Explore the murals, galleries and shops of Alberta Street.

6. Evening

   Mississippi Avenue

   Have dinner and catch live music on North Mississippi Avenue.