powell's · voodoo · salt & straw · lan su · the trolls · forest park
welcome to portlandThe food-cart-and-bookstore city. Powell's covers a full city block and has a million books. Voodoo Doughnut has a line out the door at 2 AM. Salt & Straw makes their ice cream weird on purpose. The trolls live in the parks and gardens. The bridges cross the Willamette eleven times. Portland is its own thing, and that's the point.
Best for
Food, books, gardens, weird stuff, slow weekends
Fly into
PDX · 20 min east of downtown
Stay at least
2-3 nights · 4 if you want it slow
Best time
May-Oct prime · year-round indoor scene
getting your bearings
Portland sits at the confluence of the Willamette River and the Columbia River, about 60 miles east of the Pacific Ocean. Population about 635,000 in the city, 2.5 million metro. The city is split by the Willamette running north-south, with the West Side (downtown, Pearl District, Northwest, Goose Hollow, Forest Park) and East Side (Hawthorne, Alberta, Belmont, Sellwood). Eleven bridges cross between them.
The food scene is famous. Multiple food-cart pods across the city, plus Voodoo Doughnut (open until 3 AM), Salt & Straw (artisan ice cream that started in Portland), Pine State Biscuits, the northern Thai scene on SE Division, Screen Door's fried chicken, and a thousand more. The city has more restaurants per capita than almost anywhere in America.
Portland is famous for being weird, and proud of it. The official city motto is "Keep Portland Weird" (originally borrowed from Austin). The art scene, the music scene, the bookstores, and the food carts all reflect that ethos. You'll find a giant wooden troll, a doughnut shop selling pink boxes at 2 AM, a Chinese garden, and a Japanese garden, all in the same city.
Downtown & the Pearl District: the central walkable core, with Powell's Books, Pioneer Courthouse Square, the food carts at SW 9th and Alder, and the Pearl District's gallery scene. Easy to base here for the first-time visit.
Northwest (NW 23rd): the trendy walkable shopping street with Salt & Straw, boutique shops, and Forest Park access. The "cute weekend" neighborhood.
Hawthorne (East Side): vintage shops, used bookstores, House Spirits Distillery, and the iconic Hawthorne Bridge. The "old hippie Portland" feel.
Alberta Arts District (East Side): the artiest neighborhood, with the Last Thursday street festival (the street actually closes June, July and August only, the rest of the year it moves indoors), art galleries, food trucks, and bars. The "I want art and weird" anchor.
Sellwood (Southeast): antiques, the Sellwood Bridge (one of the iconic 11), Oaks Amusement Park (1905 historic), and a quieter residential feel. The "we want kid-friendly slow" neighborhood.
In 2023 Danish artist Thomas Dambo installed six giant reclaimed-wood trolls across the Pacific Northwest as part of his "Northwest Trolls: Way of the Bird King" project. Ole Bolle at Nordic Northwest is the one Portland troll. The other five (Jakob Two Trees in Issaquah, Pia the Peacekeeper on Bainbridge, Bruun Idun in West Seattle, Frankie Feetsplinters in Ballard, Oscar the Bird King on Vashon) are scattered across the Seattle area. Each one is free to visit, with parking lots and short walks. The project celebrates Coast Salish and Scandinavian heritage. Look for colorful birdhouses in the parking lots, those are Dambo's signature signal that a troll is nearby.
Portland is best May through October. Spring brings the famous roses (Portland is the City of Roses, with the Rose Festival in early June). Summer is the prime window with long evenings, food-cart pods at their peak, and Sunday Market action. Fall (September-October) is the secret-best season, with cooler weather, smaller crowds, and the harvest food scene. Winter (November-March) is rainy and gray, but the indoor city is at its coziest with bookstores, food halls, and breweries running full-tilt.
getting there & getting around
20 minutes east of downtown on I-205 then I-84 west, or take the MAX Red Line light rail directly downtown (40 min, $2.80 one-way). The MAX is the easiest airport-to-downtown move, no traffic, drops at Pioneer Square. Uber and Lyft run $30-50 to downtown depending on traffic.
3 hours south on I-5. About 175 miles. The most-driven PNW route. Add a Olympia or Vancouver WA stop for breakfast if you're hungry.
1.5 hours from Cannon Beach via US-26. The classic Cannon Beach to Portland drive, through the Coast Range forests. Pair the coast with Portland naturally.
1 hour west on I-84. About 60 miles. The waterfall Gorge corridor between Hood River and Portland. Combine Portland with the Gorge waterfalls as one weekend.
Paid street parking ($2-3/hour) and paid garages ($15-25/day). SmartPark garages are the city-run option with the best rates. Don't drive downtown unless you have to, walk and use MAX/streetcar instead.
Four MAX lines (Red, Blue, Green, Yellow) crisscross the metro area. $2.80 single ride, $5.60 day pass via the TriMet Hop card or phone app. The cheap easy way around Portland. The Portland Streetcar loops through the Pearl District, downtown, and across the river.
Portland is the most bike-friendly large city in America. Biketown (city bike share) has 3,000 e-bikes around town, $1 to unlock plus $0.35/min. The fast easy way to get between neighborhoods, especially across the bridges.
Vans fit downtown parking garages and street parking fine. RVs over 25 ft should park at the airport area or Jantzen Beach and take the MAX downtown. Multiple Walmart locations permit overnight RV parking on the Portland metro periphery (Jantzen Beach, Hillsboro, Tigard).
the must-sees
The largest independent bookstore in the world. A full city block (around 68,000 square feet), with a million books, color-coded rooms for each section, and a cafe inside the Rose Room. Free to walk through, easy to spend 2-3 hours. Located on West Burnside between 10th and 11th. Open daily 10 AM to 9 PM, with the Rare Book Room closing at 5. Parking is paid, either the street at about $2/hr or the Brewery Blocks garage, so don't count on validation.
The pink-box Portland donut shop. Original location at 22 SW 3rd Avenue downtown, open 6 AM to 3 AM daily, plus a second location in the Pearl District. The lines can be long, but they move fast. Famous for the bacon maple bar, the Voodoo Doll, and the pink box. Donuts run about $1.50 to $6.25. They have taken cards since 2016, so ignore any older list that says cash only. The pink box is the Portland souvenir kids will lose it over.
The Portland-born artisan ice cream chain. Started in 2011 as a cart in the Alberta Arts District, now three shops in Portland proper (NW 23rd, NE Alberta, SE Division) plus Lake Oswego and Bridgeport, and a lot of cities beyond Oregon. The flavors rotate seasonally with weird-but-amazing combinations like Pear & Blue Cheese, Honey Lavender, Black Olive Brittle & Goat Cheese. Free tastings at the counter (sample as many as you want). About $6 per scoop. Alberta is where it started, NW 23rd is the one most visitors find first.
A full city block of authentic Ming Dynasty-style Chinese garden in the heart of downtown's Old Town. Built in 2000 by Chinese artisans from Suzhou (Portland's sister city), with hand-carved pavilions, koi ponds, lotus blossoms, and a teahouse. $18/adult, $17/senior, $15/kid 6-18, free under 5. Open 10 AM to 5:30 PM March through October, closing an hour earlier the rest of the year. The teahouse upstairs looks out over the koi pond and is the reason to stay longer than you planned. The unexpected quiet stop in the middle of the city.
Ole Bolle is Portland's one Thomas Dambo troll, installed 2023 at the Nordic Northwest campus. Part of the six-troll "Way of the Bird King" project that spans Portland and the Seattle area. Free to visit. A family stop that kids remember.
Ole Bolle at the Nordic Northwest campus, 8800 SW Oleson Rd, Portland (technically just over the Beaverton line). Easy to find, with free parking and a short walk through the Nordic gardens. Look for the colorful birdhouses in the parking lot. Those are Dambo's signal that a troll is nearby.
The other five Dambo trolls in the Northwest series all live in the Seattle area. Pia the Peacekeeper on Bainbridge Island. Bruun Idun and Frankie Feetsplinters in Seattle proper. Oscar the Bird King on Vashon Island. Jakob Two Trees in Issaquah. If you're hunting all six, plan a 2-day Seattle loop after Portland. See Chapter 12 for the full troll hunt route.
Portland has multiple food-cart pods clustered around the city. The downtown SW 9th and Alder pod (called The Bite on Alder) has 50+ carts in a parking lot, the most-iconic Portland food cart experience. Lunch hours are peak (11:30-1:30), plan accordingly. Cartopia at SE Hawthorne and 12th is the East Side anchor, open later for late-night eats. The Carts on Foster in Foster-Powell neighborhood is the family-friendly pod with covered seating.
5,200 acres of forest on the west side of the Willamette, with 80+ miles of trails. Portland Parks calls it the largest forested natural area inside any US city limits, and even that gets argued about, but nobody argues about the size of it. The Wildwood Trail is the spine, running 30 miles through the entire park. Pittock Mansion at 1,000 ft elevation has the panoramic Portland-plus-Mount-Hood view (free, family-friendly, 5-min walk from parking). The "we need real nature" stop right in the city.
Considered one of the most authentic Japanese gardens outside Japan. 12.5 acres in Washington Park, with five distinct garden styles, a cultural center, and views of Mount Hood from the Heavenly Falls overlook. $22.50/adult, $19.50/senior, $16.50/kid 6-17, free under 5. Open 10 to 5:30 most days, noon to 5:30 on Tuesdays. The most-recommended Portland garden for first-time visitors.
Across the river on the East Side waterfront. Hands-on science museum with a planetarium, IMAX, and the USS Blueback submarine tour. $22.50/adult, $20.50/senior, $15.50/kid 3-13, free under 3. The submarine is a separate ticket, tours every 20 minutes from 10:10 to 4:30, ages 3 and up and 36 inches minimum. Open daily. The "kids will love it and parents will too" Portland stop, especially on rainy days. Takes 3-4 hours minimum.
kids pick
The classic Portland family day. Start at Voodoo Doughnut (downtown original, get the pink box for the photo). Drive 20 min southwest to Nordia House for Ole Bolle the troll (free, paved walk, kids climb on the troll for photos). Back to downtown for Powell's Books (let kids pick a book each, with kids' books under $10, can spend 1-2 hours easily). End at Salt & Straw NW 23rd for ice cream with weird flavors (try one weird flavor + one safe flavor). The Portland day that locks in for the kids.
smaller spots most guides miss
Powell's and Voodoo get the headlines. Portland has whole layers most weekend visitors miss.
Sellwood, Southeast Portland. One of the oldest amusement parks in the country, running since 1905, on the Willamette River. Old-school rides, a roller rink, mini golf, and arcade games. Free entry, pay-per-ride or an unlimited wristband at $44.45 standard and $49.45 on peak days, less for kids under 48 inches. Rides run spring through fall, the roller rink is year-round.
30 minutes northwest of downtown. 26,000-acre agricultural island in the Columbia River, with U-pick farms, the Pumpkin Patch (October), a clothing-optional beach (north end, don't go there with kids), Topaz Farm (the old Kruger's, new name and new owners), and the historic Bybee-Howell House. The "we want farmland 30 min from downtown" escape. Free, family-friendly.
South Waterfront. A 3-minute gondola ride up 500 feet to the OHSU (Oregon Health Science University) campus. $9/adult round trip, kids 6 and under free with a paying adult. The unexpected city view, with Mount Hood on clear days. Plus the OHSU campus has a public skybridge with great views. Weekdays 5:30 AM to 9:30 PM, Saturday 9 to 5, and it does not run Sundays or holidays, which catches a lot of weekend visitors out.
Old Town/Chinatown. The biggest classic arcade and bar in Portland, with 100+ vintage arcade games and pinball machines from the 1980s-90s. Family-friendly daytime, 21+ after 5 PM. $5-10 in tokens goes a long way. The "we got rained on" indoor stop.
Washington Park. 10,000 rose bushes and 610+ varieties in the official testing garden for the American Rose Society. Free entry, peak bloom mid-June through mid-July (Portland Rose Festival is in early June). Family-friendly, easy parking. The "free Portland in bloom" stop.
Pearl District. Multiple food halls have popped up across Portland in the last few years, with rotating local vendors. Pine Street Market downtown, Ankeny Tap and Table, the Zipper East Side. The newer foodie scene beyond food carts, family-friendly, multiple options per spot.
121 SW 3rd Ave, downtown. Big-portion American breakfast in a beautiful old room, the wild mushroom scramble and the crunchy French toast. The "we want a real sit-down breakfast" Portland stop, family-friendly. Note it moved off SW Stark, so check the address. About $18-28/person.
West Burnside. 1914 historic dance hall with the original "floating" spring-loaded dance floor, owned by McMenamins. Live concerts most nights, free to walk in the lobby and see the historic photos. The "we saw something cool" Portland evening.
trails worth doing
Portland has more park acreage per capita than almost any city in America. Forest Park alone is 5,200 acres of urban forest. You can hike for hours and still be in the city.
Pittock Mansion walk
Free park · Portland skyline + Mt Hood view
International Rose Test Garden loop
Paved · 10,000 rose bushes · Washington Park
Tom McCall Waterfront Park
Paved · downtown waterfront · 11 bridges
Lower Macleay to Pittock
Forest Park entrance · waterfalls · stone walls
Council Crest summit
1,073 ft · panoramic view
Wildwood Trail (Forest Park)
Multiple sections · 30-mile main trail
Powell Butte loop
East Side park · panoramic view · meadows
Mount Tabor loop
East Side extinct volcano · city views
when you want low-key
Portland is a slow-by-default city. These are the low-energy options for between-tour days and rest mornings.
Walk every room of the original Powell's at NW 11th & Burnside. Grab something at the Rose Room cafe, settle into the reading chairs. Easy 2-3 hour stop, free, family-friendly.
The downtown Chinese garden, a full city block of it. Sit by the koi pond, walk the pavilions, read a book. The "we need to slow down" Portland anchor.
Downtown food hall with multiple rotating vendors. Everyone picks their own thing, no decision wars. Family-friendly, takes 90 minutes-2 hours.
10,000 rose bushes in Washington Park. Free, family-friendly, easy paved paths. Peak bloom mid-June through mid-July, but always beautiful in the warm months.
The downtown waterfront park along the Willamette. Watch the bridges, walk the paved path, picnic on the lawn. Free, family-friendly. Peak crowds during Saturday Market (right next to the park).
SE Hawthorne Boulevard between 30th and 45th. Multiple vintage shops, used bookstores, and the original Salt & Straw. The "old Portland" walk.
where to eat
Portland is the foodiest small city in America. Food carts, food halls, brunch institutions, fine-dining anchors, the original Salt & Straw, the original Voodoo. You can't go wrong, but you can plan smart.
Pine State Biscuits. Multiple Portland locations (Alberta, Belmont, Schuyler). The Reggie biscuit (fried chicken + bacon + cheese + sausage gravy) is iconic. Family-friendly, expect a 15-30 min wait on weekends. The most-recommended Portland breakfast. About $12-18/person.
Tasty n Daughters. N Williams. Modern American brunch with shareable plates. Family-friendly. The "we're going somewhere nice for brunch" Portland anchor. The downtown Tasty n Alder closed in 2020, so this is the one still standing. About $20-35/person.
Mother's Bistro. 121 SW 3rd Ave downtown. Classic American breakfast in a beautiful old room, family-friendly, big portions. It moved off SW Stark, so use the new address. The "comfort food brunch" Portland classic. About $18-28/person.
Screen Door. East Side at NE 31st. Southern-style brunch with fried chicken and waffles, family-friendly. Long lines on weekends. The unofficial Portland brunch line-up. About $18-30/person.
The Bite on Alder pod at SW 9th & Alder. 50+ food carts in a downtown lot, everything from Thai to Korean to BBQ to bahn mi. The classic Portland food cart experience. Each cart $8-15. Find a picnic table or take it back to a hotel.
Cartopia at SE Hawthorne and 12th. Late-night East Side food cart pod with covered seating. The "after a brewery" food stop.
The Carts on Foster in Foster-Powell. Family-friendly food cart pod with covered seating and a beer garden, the easiest pod for families with kids.
Lardo on SE Hawthorne. The sandwich shop everyone sends you to, famous for the Pork Trifecta. Family-friendly, fast, no fuss. The old downtown Lardo closed in 2024, so Hawthorne is the one to aim at. About $12-18/person.
OK Chicken & Khao Soi. 3226 SE Division. Heads up if you have an old Portland list: Andy Ricker closed every Pok Pok back in 2020, and the wings are gone with it. This northern Thai spot opened in that exact space in January 2026 and is the closest thing going. About $18-30/person.
Andina. Pearl District. Modern Peruvian with ceviche, tapas, and a great bar, family-friendly. The "we want to celebrate" Pearl District dinner. About $40-70/person.
Higgins Restaurant. Downtown. 30-year farm-to-table Portland institution with seasonal Pacific Northwest cuisine. Reservations essential. The "Portland classic fine-dining" anchor. About $50-90/person.
Le Pigeon. Burnside. The James Beard-winning chef-driven anchor with creative Pacific Northwest cuisine. Tasting menu format, reservations essential. The "we got a sitter" Portland dinner. About $90-150/person.
Apizza Scholls. SE Hawthorne. The best pizza in Portland by most local accounts, with hand-stretched Neapolitan-style crust. Family-friendly. The "we just want amazing pizza" stop. About $20-35/person.
Voodoo Doughnut. Original at 22 SW 3rd, open 6 AM to 3 AM. The pink box, the bacon maple bar, the Voodoo Doll. Cards fine. About $1.50 to $6.25 per donut.
Salt & Straw. NW 23rd, NE Alberta and SE Division. Artisan ice cream with weird seasonal flavors. Free tastings at the counter, sample as many as you want. About $6/scoop.
Blue Star Donuts. SW Jefferson (the flagship), SE Division, South Waterfront, plus a PDX kiosk. The brioche-based alternative to Voodoo, with grown-up flavors like Blueberry Bourbon Basil. They closed a pile of shops, so check the address before you drive. About $4 per donut.
Pip's Original Doughnuts. SE Fremont. Mini doughnuts made to order with house-pressed chai. The local-favorite alternative to the famous donut shops. About $5-8 for a dozen minis.
Stumptown. Multiple Portland locations. The Portland-born roaster that half the country copied. The Ace Hotel location downtown is the one everybody photographs, and it is a fine place to sit when the rain starts.
where to spread the blanket
Tom McCall Waterfront Park. Downtown along the Willamette. 2 miles of paved path, picnic lawns, the bridge views, the Saturday Market. Free, easy parking (paid garages). The most-recommended Portland picnic.
Washington Park. The main Portland park complex on the west side. Rose Test Garden picnic tables, Japanese Garden grounds, plus the Hoyt Arboretum. Free park entry, paid gardens. The "we want green and gardens" picnic.
Pittock Mansion picnic area. 5,200-acre Forest Park, at the mansion summit. Picnic tables with the panoramic Portland-plus-Mount-Hood view. Free, easy parking.
Sellwood Riverfront Park. Southeast Portland on the Willamette. Big lawn, picnic tables, river views, plus the Oaks Bottom wetlands next door. Free, easy parking, family-friendly.
Mount Tabor Park. East Side extinct volcano with multiple picnic shelters. City views from the summit, free, family-friendly. The East Side picnic anchor.
Council Crest Park. West Hills. One of the highest public points in Portland at 1,073 ft, with picnic tables and a panoramic view of five volcanoes on a clear day. Free.
amy's check
For traveling families: what's nearby and what's not. Portland is a major metro with everything.
Costco
Multiple Portland metro locations · the SE Hayden Island Costco is closest to downtown
Target
Multiple Portland metro locations · the Galleria downtown is most-walkable
Trader Joe's
Multiple Portland metro locations · the Hollywood District at NE 41st is most-recommended
Chick-fil-A
Mall 205 on SE Stark · the first one inside Portland city limits, opened January 2026 · more Vancouver WA locations 15 min north
groceries, gas & van basics
Portland is a real city with everything. The easiest resupply stop in the PNW.
Full coverage with Fred Meyer (Portland flagship), Safeway, New Seasons Market (local upscale chain), Whole Foods, Trader Joe's, WinCo Foods. New Seasons is the Portland-favorite local chain with 18 locations across the metro, similar to Whole Foods but locally-owned.
For Costco runs: multiple locations including Hayden Island, Tigard, Hillsboro, Clackamas. The Hayden Island Costco is closest to downtown.
Multiple gas stations throughout Portland. Costco gas at multiple locations. The Oregon gas rule changed in 2023, so you can pump your own now. In Multnomah County stations can run up to half their pumps as self-serve, and only while an attendant is working, so you will hit both kinds. Watch for the signs at the island and let the attendant come to you if there is any doubt. Prices comparable to Seattle.
Public restrooms at Tom McCall Waterfront Park, Pioneer Courthouse Square, Powell's Books, plus all city parks (Washington Park, Mt Tabor, Sellwood). Drinking fountains throughout downtown and along the waterfront. Most cafes, bookstores and breweries have restrooms for customers.
RV dump stations at Jantzen Beach RV Park ($15 non-guests), Portland Fairview RV Park, and Crown Point RV Park. No free public dumps in the city. Public trash bins at all parks and most downtown corners.
Base downtown for the first-time Portland visit. Walk to Powell's, the food carts, Pioneer Courthouse Square, Lan Su Garden, the waterfront. Take MAX or Uber to East Side neighborhoods. The walking access is what makes downtown the smart base.
For families: Base in Northwest Portland (NW 23rd area) for the second-time visit. Walking distance to Salt & Straw original, the Pearl District, Forest Park trails, and Washington Park. Quieter than downtown, more residential feel, family-friendly hotels.
For van or RV travelers: Base at Jantzen Beach RV Park (north Portland), take MAX or Uber downtown. Don't try to take a van or RV into downtown Portland streets, parking is tight and one-way streets are tricky.
hotels, B&Bs & van
Portland has hotel variety as a major city. Historic downtown landmarks, modern boutique design hotels, family-friendly chains, plus full RV parks. Festival weekends (Rose Festival in June, Pride in June, Waterfront Blues Festival in July) book 3-6 months ahead.
Budget · $130-$200/night
The "we just need a bed in Portland" tier
Hyatt Place Portland Downtown. Walking distance to Powell's, Pearl District, food carts. Reliable chain, free breakfast, family-friendly. About $140-$200/night.
Holiday Inn Express Portland Downtown. Couple blocks from MAX. Free breakfast, indoor pool, family-friendly, walking distance to downtown. About $130-$190/night.
The Mark Spencer Hotel. Downtown. Boutique-budget combo, kitchenettes, walking distance to everything. About $140-$200/night. The under-rated downtown budget pick.
Mid-range · $200-$350/night
Real character, real downtown
Hotel Lucia. Downtown. Boutique art-hotel with the famous Imogen Cunningham photo collection, walking distance to Powell's. About $220-$320/night. The "we want artsy but reliable" choice.
The Hi-Lo Hotel. Downtown. Modern design hotel in a 1910 historic building, with a great on-site restaurant (Pearl Tavern). About $240-$340/night.
The Heathman Hotel. Downtown. 1927 historic luxury hotel with the famous library (50 Shades of Grey was partly set here). Family-friendly, walking distance to everything. About $280-$400/night.
Splurge · $400-$700/night
When you want the full Portland experience
The Nines. Downtown atop the historic Meier & Frank building. Luxury hotel with the famous atrium, multiple restaurants, walking distance to everything. About $350-$550/night. The most-iconic Portland luxury stay.
Hotel deLuxe. Downtown. Hollywood-glamour-themed boutique with the famous Driftwood Room bar. About $300-$500/night.
The Bidwell Marriott. Pearl District. Modern luxury with floor-to-ceiling windows, walking distance to Pearl District galleries and food. About $300-$500/night.
Vrbo and Airbnb have lots of options in downtown, NW Portland (23rd Ave area), Hawthorne, Alberta, Sellwood, and the Pearl District. Downtown lofts are family-friendly options for 4-6 at $200-$450/night. NW 23rd Victorian houses are the splurge family option, $400-$700/night. Book 1-2 months ahead for summer weekends.
Van life · campgrounds
Multiple state, county, and private RV options
Jantzen Beach RV Park. North Portland, walkable to MAX line. Full hookups, $55-$80/night. The most-recommended Portland-adjacent RV park, on Hayden Island.
Portland Fairview RV Park. East Portland near the airport. Full hookups, family-friendly, $60-$85/night.
Crown Point RV Park. Corbett, 25 min east of Portland near the Columbia Gorge. Pretty rural setting with hookups, $50-$75/night. The "we want to also do the Gorge" option.
Where you can't sleep: No overnight on downtown streets or downtown parking lots, Walmart in Jantzen Beach and Hillsboro permit overnight RV, most Portland parks prohibit overnight.
The Nines, Heathman, Hotel deLuxe: 2-3 months ahead for summer weekends. Rose Festival (early June) books 4-6 months ahead.
Hyatt Place, Holiday Inn Express: 4-6 weeks ahead for summer weekends usually works.
Vacation rentals: 2-3 months ahead for summer (July-August), 1-2 months ahead for shoulder seasons.
Jantzen Beach RV Park: 2-3 months ahead for summer weekends. The most-booked Portland RV park.
Restaurant reservations: 2-4 weeks ahead for Le Pigeon, Andina and Higgins. 1 week ahead for most other Portland sit-downs.
Festival weekends to plan around: Rose Festival (early June), Portland Pride (mid-June), Waterfront Blues Festival (July 4th weekend), Last Thursday on Alberta (the street-closure version runs June, July and August).
Shoulder season (March-April, October-November): 2-3 weeks ahead usually fine. The best value time to visit Portland, with the indoor food scene at its peak.