The Great Milwaukie Pumpkin Hunt turns downtown into a free seasonal puzzle October 2 through 24.

Ten hand-blown glass pumpkins are hidden in public locations, with clues helping residents explore storefronts, public art and familiar blocks from a new angle.

Households should claim only one pumpkin, and searchers never need to enter private property, climb or move objects.

The celebration expands October 10 and 11 at Canned Heat Glass Studios, where live demonstrations and hundreds of fall glass pieces are planned from 10 a.m. to 5 p.m.

Storefront decorations continue throughout October, followed by Trick or Treat on Main Street from 1 to 3 p.m. October 31.

Check the current clue before leaving, wear comfortable shoes and treat the hunt as a downtown outing even if another neighbor reaches the pumpkin first.

Milwaukie Farmers Market continues from 9:30 a.m. to 2 p.m. Sundays through October 25 at Main and Harrison.

The final fall markets bring seasonal produce, orchard fruit, baked goods, prepared foods, cheese, meat, plants and locally made gifts.

Live music and food stands also make the market a relaxed meeting place for friends or families planning an autumn brunch.

Arrive early for the broadest harvest selection or later for a slower lunch-and-music visit.

Walking, biking, local buses and the nearby MAX Orange Line can reduce parking pressure around downtown.

Bring reusable bags, consider a cooler for perishable purchases and carry a backup payment option.

Vendor attendance and harvest inventory can change weekly, so confirm current information when one particular product is driving the trip.

1847 Food Park brings eleven food carts, shared seating and a multi-level taphouse to 1925 SE Scott Street.

The varied lineup lets every member of a group order independently while still gathering around one table.

Indoor seating, covered areas, heaters and fire features help the venue work during cooler Milwaukie weather.

The family- and pet-friendly park is generally open noon to 9 p.m. Sunday through Thursday and until 10 p.m. Friday and Saturday.

Individual cart schedules can differ from the park’s overall hours, so confirm a favorite vendor before visiting.

Guests managing allergies should discuss ingredients and cross-contact directly with each cart.

Arrive before the dinner rush for easier group seating, bring a warm layer and consider pairing the meal with a downtown or riverfront walk.

pFriem Milwaukie serves seasonal food and craft beverages inside the restored 1938 City Hall at 10722 SE Main Street.

The former civic building once housed city offices, police services and the fire department, giving today’s dining room unmistakable local character.

The rotating menu has included burgers, macaroni and cheese, Pacific Northwest seafood, salads and desserts.

Keeper Coffee shares the building, making the location useful for groups with different tastes and for earlier meet-ups.

Daily hours run from 11:30 a.m. to 9 p.m., while an upstairs dining room can accommodate gatherings when available.

Check current menus, tap lists and event-space details before visiting, especially when one item or room is central to the plan.

Consider extending the outing with a downtown walk.

The Trolley Trail gives Milwaukie walkers and cyclists a roughly six-mile route along a former streetcar corridor toward Gladstone.

Paved and gravel sections support everything from a quick neighborhood stroll to a longer point-to-point ride.

Nearby North Clackamas Park adds about 1.7 miles of trails, mature trees, waterways, restrooms, picnic areas and playgrounds.

Fall visitors should prepare for earlier darkness, wet leaves and debris after windy weather.

Bring water, a light layer and visible gear, and use footwear with dependable traction.

Cyclists should carry lights and a basic repair kit, while dog walkers need a leash and waste bags.

Choose a turnaround point that suits the whole group, keep right on shared paths and check current park or trail conditions before leaving.

Two harvest festivals near Milwaukie offer different styles of fall day trip.

Frog Pond Farm in Wilsonville runs through November 1 with animals, a corn maze, play areas, bounce attractions and weekend llamas.

General admission is listed at $16 for visitors age two and older, with some items and experiences priced separately.

Liepold Farms in Boring operates its 2026 festival through October 31 with pumpkins, seasonal produce and an adventure corn maze.

Choose Frog Pond for energetic children and animal encounters, or Liepold for a more traditional maze-and-pumpkin outing.

Check current hours, tickets, attraction access and weather notices before driving.

Wear sturdy closed-toe shoes, prepare for mud and review accessibility information when anyone in the group uses a stroller or mobility device.