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Portland New Year's Eve route inspiration

Portland New Year's Eve

A drone countdown, old taverns, a forest walk

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3 days through Downtown Portland, Northwest Portland.

Portland New Year's Eve is a 3-day curated route with 2 destinations and 15 places to eat, see, and do. Preview stops and timing, then plan it in TripsCircle.

  1. 1
    Downtown Portland on the Portland New Year's Eve route

    Destination 01

    Downtown Portland

    9 places

    Two nights downtown for old dining rooms, the Square's countdown and live music.

    • NYE drone show at Pioneer Courthouse Square near Downtown PortlandPhoto: Visitor7 · CC BY-SA 3.0

      NYE drone show at Pioneer Courthouse Square

      The city's free NYE party fills 'Portland's Living Room' with a DJ, a 9 pm family drone show and a midnight countdown show.

      Tip Food and drinks are sold inside; arrive early for space near the steps.

      DoDowntownFree4 hr8 pm to 12:30 am
    • Tom McCall Waterfront Park near Downtown PortlandPhoto: Taken by User:Cacophony. · CC BY-SA 2.5

      Tom McCall Waterfront Park

      The riverside park along the Willamette, with the downtown skyline on one side and lit bridges on the other.

      Tip Walk it at night between dinner and the Square.

      SeeDowntownFree45 minNight
    • Eastbank Esplanade near Downtown PortlandPhoto: Tony Webster · CC BY 2.0

      Eastbank Esplanade

      Riverside path on the east bank with the best straight-on view of the downtown skyline over the water.

      Tip Cross the Hawthorne or Steel Bridge on foot for the classic skyline view.

      SeeCentral EastsideFree45 minBlue hour
    • Huber's Cafe near Downtown PortlandPhoto: Visitor7 · CC BY-SA 3.0

      Huber's Cafe

      Portland's oldest restaurant, founded in 1879, known for roast turkey and Spanish coffee flamed at the table.

      Tip Sit at the bar to watch the Spanish coffee pours.

      EatDowntown$$1.5 hrDinner
    • Jake's Famous Crawfish near Downtown PortlandPhoto: Visitor7 · CC BY-SA 3.0

      Jake's Famous Crawfish

      Seafood house dating to 1892, with dark wood, white tablecloths and Pacific Northwest oysters and salmon.

      Tip Book for Dec 30 or an early Dec 31 seating.

      EatWest End$$$2 hrDinner

    • Andina

      Family-run Peruvian restaurant in the Pearl District since 2003, with ceviches, small plates and pisco cocktails.

      Tip Reserve early for NYE; the bar takes walk-ins.

      EatPearl District$$$2 hrDinner
    • Crystal Ballroom near Downtown PortlandPhoto: Steve Morgan · CC BY-SA 4.0

      Crystal Ballroom

      McMenamins' 1914 ballroom with a sprung 'floating' dance floor, which books a ticketed NYE concert most years.

      DrinkWest End$$4 hrLate

    • Departure

      Rooftop restaurant and lounge atop The Nines, with covered, heated terraces over downtown; it typically throws a NYE party.

      Tip The terraces are covered and heated, so rain is not a dealbreaker.

      DrinkDowntown$$$2 hrLate

    • The Nines

      Hotel in the upper floors of the 1909 Meier & Frank Building, directly across from Pioneer Courthouse Square.

      Tip The closest bed to the countdown; Departure is upstairs.

      StayDowntown$$$$
  2. 2
    Northwest Portland on the Portland New Year's Eve route

    Destination 02

    Northwest Portland

    6 places

    The forested West Hills and NW 21st for a first-day hike and a slow brunch.

    • Lower Macleay Trail and the Stone House near Northwest PortlandPhoto: Finetooth · CC BY-SA 3.0

      Lower Macleay Trail and the Stone House

      Creekside trail into Forest Park past the mossy 1930s WPA Stone House, known locally as the Witch's Castle.

      Tip Start at Lower Macleay Park, NW 29th and Upshur.

      OutdoorsForest ParkFree1.5 hrMorning
    • Wildwood Trail, Forest Park near Northwest PortlandPhoto: EncMstr · CC BY-SA 3.0

      Wildwood Trail, Forest Park

      The 30-mile spine of one of the largest urban forests in the US, under Douglas fir and bigleaf maple.

      Tip Follow it uphill from Lower Macleay to reach Pittock Mansion.

      OutdoorsForest ParkFree2 hrMorning
    • Pittock Mansion near Northwest PortlandPhoto: Steven Pavlov · CC BY-SA 4.0

      Pittock Mansion

      1914 French Renaissance mansion high in the West Hills; its lawn looks over downtown to Mount Hood.

      Tip The house is closed Jan 1, but the grounds and viewpoint stay open.

      SeeWest HillsFree45 minClear morning
    • Powell's City of Books near Northwest PortlandPhoto: Michael Barera · CC BY-SA 4.0

      Powell's City of Books

      A full city block of new and used books, color-coded rooms and a rare book room, on the edge of the Pearl.

      Tip Grab a map at the entrance; check holiday hours for Jan 1.

      ShopPearl District$75 minAfternoon

    • Besaw's

      Northwest Portland restaurant founded in 1903, now a brunch standby on NW 21st.

      Tip Expect a wait on Jan 1; put your name in and walk NW 21st.

      EatNorthwest District$$75 minBrunch

    • Ken's Artisan Bakery

      Ken Forkish's bakery on NW 21st since 2001, known for croissants, canelés and country loaves.

      Tip Go early; pastries sell out by midday.

      EatNorthwest District$30 minMorning

The moments that shape this trip.

Planning Portland New Year's Eve.

Portland has no New Year's fireworks; the city's free countdown is a drone show over Pioneer Courthouse Square, the downtown plaza still lit for the holidays. Arrive Dec 30 for a flaming Spanish coffee at Huber's and seafood at Jake's. On Dec 31 eat at Andina in the Pearl, then choose between the Square's dance party and midnight drones, a ticketed show at the Crystal Ballroom, or the rooftop at Departure. Jan 1 is a walk up the Lower Macleay Trail past the Stone House to Pittock Mansion's view of the city and Mount Hood, then brunch on NW 21st and an hour in Powell's.

Good for Couples and friends who want a low-key countdown, good food and a real walk on Jan 1.

When to go

The free Pioneer Courthouse Square celebration has run two years: on NYE 2024 a DJ dance party ran 8 pm to 12:30 am with drone shows at 9 pm and midnight, and NYE 2025 repeated the 8 pm party, 9 pm drones and midnight countdown with about 250 drones and no fireworks. Personal fireworks are illegal in Portland. Dec 31 is typically cold and wet, around 40 F, with rain more likely than snow; bring a waterproof layer. Ticketed shows at the Crystal Ballroom and rooftop parties sell out. Pittock Mansion's house is closed Jan 1, though the grounds and viewpoint are open; check holiday hours at restaurants.

Getting around

Downtown, the Square, Huber's, Jake's, the Crystal Ballroom and Powell's are all within a 15-minute walk. TriMet and the Portland Streetcar ran free after 8 pm on NYE 2025, and MAX stops right at the Square. Rideshare surges after midnight; use the free transit. For Jan 1, the Lower Macleay trailhead is at NW 29th and Upshur, a short ride from downtown; the climb to Pittock Mansion is about 2.5 miles one way and muddy in winter. PDX airport is about 40 minutes by MAX Red Line.

Tips for your crew

  • Drone shows use no smoke or explosions, so the view from inside the Square matters; arrive by 11:30 pm.
  • Order the Spanish coffee at Huber's; it is flamed tableside and the reason people go.
  • Wear boots with grip for Lower Macleay on Jan 1; the trail is rooty and wet in winter.

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