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October brings crisp fall days, festive nights, and plenty of reasons to explore the Peninsula. From pumpkin season and Halloween celebrations to outdoor markets, art festivals, hands-on workshops, and community traditions, the calendar is packed with ways to celebrate autumn close to Bay Meadows.

Get into the spirit with Nightfall at Filoli, the Half Moon Bay Art & Pumpkin Festival, haunted happenings at Hiller Aviation Museum, and trick-or-treating throughout the Peninsula. Or slow things down with a farmers market stroll, a scenic hike, a baking class, or a Saturday spent browsing local makers. With so much happening in San Mateo and beyond, October is the perfect time to get out, connect, and enjoy everything the season has to offer. We want to see your season! Show us your spooky decorated stoops, the stunning colors of our neighborhood landscape, your fall harvest in Persimmon Park, plus favorite seasonal sips at Blue Bottle Café and bites in Town Square.

Be sure to invite us to collaborate and tag us at @baymeadowslife in your autumn Instagram photos this fall.

When you live just steps from Caltrain, getting from here to there is easy and car-free. Grab the Hillsdale Caltrain schedule and dive into our monthly event roundup to discover all the ways to celebrate, create, explore, and connect throughout the month ahead.

Bay Meadows Run Club with Basecamp San Mateo. Join this free fun run Wednesday evenings at 6pm and Saturday mornings at 8am. Meet at 3050 S. Delaware for a 2-, 3-, 4- or 6-mile loop (something for everyone) to get moving. Run, jog, or walk. Happening weekly – rain or shine. All paces and people are welcome. Members often gather in Town Square for a Blue Bottle coffee or at Fieldwork Brewing Beer Garden after each run. Plus, there’s no fee! You heard right – membership is not required. This is a community building fun run, compliments of our neighbors at Basecamp Bay Meadows.

Sunday Downtown San Mateo Farmers Market. West Coast Farmer’s market runs year-round at 222 East 4th Avenue Sundays from 9am to 2pm in Downtown San Mateo. The farmer’s market has a curated selection of fresh fruits, veggies, and a couple of tasty food trucks to fuel your morning stroll.

College of San Mateo Farmers’ Market. Shop seasonally and fresh each Saturday from 9am to 1pm (year-round) at San Mateo’s largest farmer’s market located at 1700 West Hillsdale Boulevard.

The 25th Avenue in San Mateo Farmers’ Market. May through October 20 on Tuesdays from 3pm to 7 pm, this farmers market is an easy walk or bike ride from Bay Meadows (~0.8 mi), bringing the best Peninsula produce and makers moments from your door.

October 2, First Friday Nights. On the first Friday of every month, from 5 PM until 8 PM, parents and kids celebrate together at CuriOdyssey in San Mateo. Dance to some of your favorite hits, while enjoying animal presentations and science activities.

October 2, Movies in the Park. Catch School of Rock under the stars at Barrett Community Center in Belmont, with movie snacks, raffle prizes, and plenty of outdoor movie night fun.

October 2, San Mateo County History Museum FREE First Fridays. Visit the SMCHM every Friday for free First Friday events, where children enjoy special programs including crafts and storytime, and adults can join a docent-led tour of the museum.

October 4, Autumn Succulent Terrarium Workshop. Create a festive pumpkin-shaped succulent terrarium, perfect for your autumn décor, at this hands-on seasonal workshop in San Mateo.

October 6, Marsh Hike at Coyote Point. Explore Coyote Point’s vibrant wetlands in San Mateo on a guided CuriOdyssey hike featuring native plants, local wildlife, and seasonal discoveries.

October 10 & 11, San Carlos Art & Wine Faire. Discover handcrafted art, local flavors, wine, brews, live entertainment, and family fun at the 34th Annual Art & Wine Faire in downtown San Carlos.

October 11, Croissant & Pain au Chocolat. Learn the art of classic French croissants and pain au chocolat in a hands-on baking class at Baking Arts in San Mateo.

October 17, HEAD WEST Marketplace. Spend the day exploring Downtown San Mateo’s B Street during the HEAD WEST Marketplace, where you can shop handcrafted goods from local makers and artists while enjoying the neighborhood’s vibrant retail shops and dining scene.

October 17–18, Half Moon Bay Art & Pumpkin Festival. Celebrate fall at the 54th Annual Half Moon Bay Art & Pumpkin Festival, kicking off with the legendary World Championship Pumpkin Weigh-Off.

October 23-November 1, Halloween Haunted Hangar. Come in costume and see the Gallery decked out in its spooky Halloween decorations and the “Great Pumpkin” Scavenger Hunt at the Hiller in San Carlos.

October 24, Belmont Centennial Fest. Celebrate Belmont’s 100th birthday at Twin Pines Park with a car parade and show, live music, food trucks, games, a time capsule ceremony, and an evening drone show.

October 24, Boos and Brews on B Street.Celebrate Halloween at Boos on B Street in Downtown San Mateo with trick-or-treating, crafts, music, food, and festive photo ops along the B Street Pedestrian Mall.

October 24, Halloween Spooktacular. Enjoy a spooktacular day in Redwood City with carnival games, a monster maze, creepy crafts, a haunted ambulance, mini pumpkin patch, prizes, and more Halloween fun.

October 28, Belmont Boo Bash. Celebrate Halloween at Belmont’s Boo Bash with Trunk or Treat, a haunted house, live music, food trucks, and festive fun for all ages in Belmont.

October 29, Trunk or Treat. Get ready for a spooktacular evening at the Hiller Aviation Museum’s Trunk or Treat in San Carlos, part of our annual Halloween Haunted Hangar celebration.

October 31, Pumpkin Drop.Join a special celebration of Halloween excitement as the Hiller Aviation Museum’s witch drops her doomed pumpkin from a high flying helicopter at the Hiller in San Carlos!

Thru November 1, Nightfall. Step into Filoli after dark for a haunting Halloween adventure filled with pumpkins, firelight, mysterious clues, an enchanted mansion, glowing woodlands, and a hidden witch’s village.

Sep-Oct Sessions at Clayroom. When signing up for 6-week classes, one signs up by selecting (signing up for) the 1st class. Classes 2-6 will occur on a weekly cadence during the same day of the week and timeslot. 6-week in-studio classes for pottery.

Discount Tuesday (at Cinemark Century San Mateo 12). There’s never been a better time to turn up on a weekday, because every Tuesday at Cinemark is Discount Tuesday—cheap movie tickets are always within reach.

Bel Mateo Bowl Friday, Saturday and Sundays in San Mateo.
Karoake – Fridays from 7:30 – 11:30pm hit the mic with friends for some Karaoke.
Planet Bowling – Bowl in the dark under black lights on Fridays from 9:30 – 11:30pm and Saturdays from 8- 11:30pm.
Incredibowl – Fridays 9:30 – 11:30pm and Saturdays from 8 – 11:30pm interactive graphics elevate your bowling game with Incredibowl.
Family Pizza Night – Sundays from 5-8pm Family Pizza Nights and all you can bowl 8-10pm!
All You Can Bowl – Sundays enjoy unlimited bowling for 2 hours 8- 10pm! 

Bicycle Sundays. From 9am – 3pm, a 3.8-mile segment of Cañada Road along Crystal Springs Regional Trail is closed between the Filoli entrance and Highway 92 allowing for non-motorized activities including jogging, bicycling, hiking, roller-skating, and walking. Cañada Road between Edgewood Road to the Filoli entrance will remain open to vehicles. Check for holiday closures.

Experience Midurban life. Bay Meadows is a family-friendly neighborhood with lots of open space to enjoy all-year long. Whether it’s growing your own vegetables in an organic community garden, playing a game of pick-up basketball after work, team building over bocce in the beer garden, picnicking with family on warm summer nights or with a run around the park, there’s no shortage of green space to explore. Check out life out and about at Bay Meadows by following us on Instagram.