Portland, Hillsboro, Cannon Beach, and Columbia River Gorge Trip

Arrival and check-in

• 12:00–2:00 p.m. | Portland International Airport to Hampton Inn & Suites Portland/Hillsboro — After landing, allow about 1.5–2 hours for rental-car pickup and the drive west to the hotel near Evergreen Parkway. Traffic can slow on the way out of Portland, so treat that as a flexible window. Check in, drop your bags, and take a breather.

Afternoon and evening

• 3:30–4:15 p.m. | Orenco Woods Nature Park — A free, easy leg-stretch among wetlands and wooded paths, with a pleasant change of pace after the flight. The trails are open daily; daylight is shortening in October, so keep the walk relaxed and head out before dusk.
• 4:30–6:00 p.m. | Orenco Station — Drive a few minutes to this walkable neighborhood and wander around Orenco Station Plaza. Pick a casual dinner nearby; budget roughly $12–$25 per person. Check restaurant hours on the day, since early-evening schedules can vary.
• 6:00 p.m. onward | Hotel downtime — Head back to the hotel, get settled, and keep the evening open for rest. No need to make the first night ambitious.

Morning

• 8:15–9:30 a.m. | Hillsboro to downtown Portland — Take the MAX Blue Line toward downtown; allow about 50–65 minutes, plus time to reach the station. A contactless card or the TriMet Tickets app works for the fare.
• 10:00–11:30 a.m. | Powell’s City of Books — Start when the Pearl District flagship opens and give yourself time to get happily lost among the color-coded rooms. It’s free to browse; set a meeting point if your group tends to split up.

Afternoon

• 11:30 a.m.–12:00 p.m. | Travel and quick lunch — Grab something casual downtown before heading uphill; a rideshare is the simplest way to keep the afternoon on track.
• 12:00–1:15 p.m. | Pittock Mansion — Explore the historic house and take in the views over Portland. Check current Thursday hours and admission before you go; the uphill location makes rideshare or driving more practical than walking from downtown.
• 1:30–2:15 p.m. | International Rose Test Garden — Stroll the free garden in Washington Park. October is well past peak bloom, but the hillside setting and city views are still worth the stop.
• 2:30–4:00 p.m. | Portland Japanese Garden — Allow time for the paths, ponds, and cultural exhibits. Admission is paid; check current hours and reserve ahead if timed entry is required. The two gardens are close, but leave a little buffer for walking between entrances.

Evening

• 5:30–7:00 p.m. | Screen Door Eastside — Head to the Kerns neighborhood for Southern-style comfort food; budget roughly $18–$30 per person before drinks and tip. A wait is possible, so check current Thursday service hours and consider joining the waitlist before you arrive. From there, use local transit or a rideshare back toward downtown to connect with the MAX Blue Line to Hillsboro; check the evening schedule before dinner so you know your last convenient train.

Morning

• 7:30–9:30 a.m. | Drive from Hillsboro to Cannon Beach — Head west on US-26; allow about 1¾–2¼ hours, depending on traffic and weather. Check road and coastal conditions before leaving, and bring a warm, waterproof layer—the coast can be windy even when town feels mild.
• 9:30–11:00 a.m. | Haystack Rock — Walk the beach and enjoy the view of this landmark sea stack. Tide pools are best at low tide, so check the tide table for your visit; stay off wildlife and give shorebirds plenty of space.

Midday

• 11:00 a.m.–12:00 p.m. | Cannon Beach History Center & Museum — Stop in downtown for a compact introduction to local coastal and Indigenous history. Hours can vary by season and day, so confirm Friday opening before you go; if it’s closed, use the time to browse nearby galleries and shops, then return if it opens later.
• 12:00–1:30 p.m. | Cannon Beach downtown and lunch — Wander the galleries and independent shops around Hemlock Street, then pick a casual café or counter-service spot. Budget roughly $15–$30 per person for lunch; check menus before settling in if you’re keeping costs low.

Afternoon and return

• 1:45–3:15 p.m. | Ecola State Park — Drive north for forest trails and sweeping coastline viewpoints. Check current park access and conditions before heading up; allow for a short walk, and budget for a possible day-use parking fee. 3:15–5:30 p.m. | Return to Hillsboro — Leave the coast by mid-afternoon for a more relaxed drive back on US-26, with extra time for rain or traffic. Allow about 1¾–2¼ hours; the coastal drive is especially tiring after a full day, so take a break if needed.

Morning

• 8:45–9:30 a.m. | Insomnia Coffee Company — Ease into the day with coffee and a light breakfast in Hillsboro; budget about $6–$15 per person. Check the specific location’s Saturday hours before setting out, and keep breakfast relaxed after yesterday’s coast trip.
• 9:45–10:45 a.m. | Rood Bridge Park — Take an easy riverside walk among the trees. It’s a good low-key reset before the wedding; wear shoes that can handle damp paths, especially after rain.

Late Morning and Afternoon

• 10:45 a.m.–12:15 p.m. | Hotel rest and wedding preparation — Head back to the hotel to change and gather what you need. Leave a little flexibility for traffic and venue parking.
• 12:15–1:00 p.m. | Drive to Hidden Creek Community Center — Allow time to park and find the event space; confirm the couple’s arrival and parking instructions rather than relying on the venue’s general parking setup.
• 1:00–9:00 p.m. | Wedding at Hidden Creek Community Center — Enjoy the celebration. If you’ll need anything specific for the event, bring it from the hotel so you won’t have to make an extra stop.

Evening

• 9:00–9:30 p.m. | Return to the hotel — Drive back to Hampton Inn & Suites Portland/Hillsboro and call it an early night if you can; tomorrow’s waterfall outing starts early.

Morning

• 6:30–7:30 a.m. | Drive from Hampton Inn & Suites Portland/Hillsboro to Carver Cafe — Leave early for the southeast drive to Damascus; allow about 45–60 minutes, with a little buffer for morning traffic.
• 7:30–8:30 a.m. | Breakfast at Carver Cafe — A hearty, casual stop; budget about $12–$25 per person. Sunday hours can change, so check before you leave.
• 8:30–9:30 a.m. | Drive to Vista House at Crown Point — Follow the Gorge route toward Crown Point; allow about 45–60 minutes.
• 9:30–10:15 a.m. | Vista House at Crown Point — Take in the sweeping Columbia River views from the grounds. The historic building’s hours may be limited in October, so check ahead; the viewpoint is the main draw regardless.

Late morning and afternoon

• 10:15–10:55 a.m. | Drive to Multnomah Falls — Allow about 30–40 minutes and check current parking and access rules before setting out; any required permit or timed-entry arrangement needs to be secured in advance.
• 10:55 a.m.–12:45 p.m. | Multnomah Falls — Enjoy the main viewpoint and lower trails, taking care on wet, slippery paths. Keep the hike modest so you have a comfortable airport buffer.
• 12:45–1:25 p.m. | Drive to Troutdale — Allow about 30–40 minutes.
• 1:25–2:25 p.m. | Casual lunch in Troutdale — Pick a relaxed local spot and budget about $12–$25 per person.

Airport and departure

• 2:25–3:10 p.m. | Drive to Portland International Airport — Allow about 30–45 minutes, then refuel and return the rental car. Aim to be at the airport around 7:00 p.m. for the 10:00 p.m. flight, leaving a generous cushion for the car return and terminal transfer. If the day runs late, shorten the falls visit rather than cutting into airport time.