Overview
The Half Moon Bay Art & Pumpkin Festival runs one weekend every October (typically the third weekend) on historic Main Street between Mill and Spruce Streets. Free admission, 250+ artists and fine craftmakers, live music on multiple stages, pumpkin carving by master carver Farmer Mike, and the Great Pumpkin Weigh-Off (which happens Monday before the festival weekend on the IDES Grounds). Attendance routinely tops 250,000 over two days, which makes traffic management the central planning challenge for any family coming by car.
How to Do It
The fastest way in and out is SamTrans bus service, which drops riders directly at the festival entrance. From the Peninsula, take SamTrans routes that serve Half Moon Bay along Highway 92 or Highway 1 — check samtrans.com for festival weekend schedules, which add additional runs. No parking to find, no sitting in bumper-to-bumper traffic on Highway 1 for an hour.
If driving, the main parking area is at the south end of Main Street where Higgins-Purissima Road meets Highway 1. Additional lots are operated by local non-profits (nominal fee, cash common) near Our Lady of the Pillar Church on Kelly Avenue and the Community Center/Shoreline Station complex, also on Kelly. Accessible parking is on Purissima Street between Correas and Kelly. Arrive before 9 a.m. if you want a reasonable spot — by 10 a.m. on a festival Saturday the approach roads are backed up from the highway.
Secure stroller and bicycle parking is at the Straight Wheel Cycling lot at the corner of Kelly Avenue and Purissima Street, with a free filtered water refill station at the same location. The festival layout spans several city blocks, and the crowd density by late morning makes strollers difficult to move through — the official tip is to backpack young children and leave the stroller at the secure parking area.
Tips & Tricks
Saturday before noon is the sweet spot. The parade runs Saturday morning and draws the biggest crowds to the parade route; if you want to see it, arrive early and claim a curb spot. If you're skipping the parade, Sunday morning is often noticeably calmer than Saturday afternoon and the vendor lines are shorter.
The Great Pumpkin Weigh-Off — where growers bring giant specimens to compete for world records — happens on the Monday before the festival weekend on the IDES Grounds, not on Main Street during the festival itself. If your kids are interested in the rhinoceros-sized gourds, the Weigh-Off is worth a separate trip; the champion pumpkin is then displayed with a photo opportunity during the festival weekend to benefit the Cabrillo Education Foundation.
The kids' costume contest runs Saturday at 10 a.m. in front of the HMB Library at 620 Correas Street. Pumpkin carving starts at 10 a.m. on the IDES Grounds. Check the schedule at hmbpumpkinfest.com before you go — specific contest times are confirmed a few weeks out.
Coastal weather in October is unpredictable in both directions. The Coastside can flip from warm and sunny to cold and foggy within an hour. Pack layers, sunscreen, and a wind layer for the kids regardless of how the morning starts.
Planning
Festival admission is free. Parking fees vary by lot: main lots run by non-profits charge a nominal fee (typically $5–15 cash), and free street parking exists on several side streets but fills by 9 a.m. SamTrans bus is the best cost and logistics choice for families.
The festival runs 9 a.m. to 5 p.m. on both Saturday and Sunday of the designated October weekend (check hmbpumpkinfest.com for the specific dates each year — 2025 was October 18–19). No pets allowed, strictly enforced by San Mateo County Sheriff. A diaper-changing and nursing rest area is available at the Community United Methodist Church at the corner of Miramontes and Johnston Streets, one block east of Main Street.
Bring a tote bag for art purchases, small bills for food and craft vendors, layers, sunscreen, and water bottles (free refill station at the Kelly/Purissima lot). Best for ages 2 and up — under 2 in a backpack carrier rather than a stroller. The festival works best for kids who can walk and engage with the environment; the sensory load is high and the crowd is real.