Bay Meadows

October is filled with fall fun activities to add to your agenda! Celebrate the new season at a local pumpkin patch, wreath workshop, wine dinner, having some Halloween fun and much, much more at Bay Meadows and beyond. When you live just steps from Caltrain it’s easy to get from here to ‘there’ car-free! Get the Hillsdale Caltrain schedule here. Explore our roundup and plan your month.

Through October 31, ABC Pumpkin Patch in San Carlos. This pumpkin patch offers large outdoor inflatables, paint ball range, games and more.

Through October 31, Arata’s Pumpkin Farm, Labyrinth Hay Maze, Petting Zoo & Haunted Barn. Half Moon Bay hay rides, pony rides & train rides, too.

Through October 31, Lemos Farm Pumpkin Patch, Petting Zoo & Haunted House. Featuring a slew of activities for the little ones in Half Moon Bay.

October 1, 8, 15, 22 and 29 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. Fall produce is here! The farmers’ tables are filled with Brussels sprouts, onions, sweet potatoes, apples, figs, pears, and so much more. Find flowers, baked goods, gourmet foods, honey, and everything you need for fall gatherings.

October 1, Dia de los Muertos. Free community event at Dr. Martin Luther King, Jr. Park with a car show, dance performances, farmer’s market, music, face painting and more.

October 1, Taste of the County. Take part in this endearing community spirit and enjoy delicious samplings from the same amazing restaurants at the San Mateo County Event Center.

October 2, Grapevine Succulent Wreath Workshop. ​Celebrate the beginning of fall by crafting a fall grapevine wreath that will last through the holidays! Once you’re finished enjoying your wreath, you can plant your succulent cuttings into container gardens or into the landscape.

October 3, Laurel Glen Vineyard Wine Dinner. A winemaker dinner featuring the wines of Laurel Glen Vineyard paired with a seasonal menu in Woodside.

October 4, 11, 18 and 25. 25th Avenue Certified Farmers’ Market. Head to downtown San Mateo Tuesdays 3 -7pm at 194 W. 25th Ave through October for an afternoon shopping the market and follow with an evening out dining downtown. Don’t forget to pick up some Sunchokes this season! Apples, figs, and grapes are also here, along with winter squash, root veggies, leafy winter greens, and so much more.

October 7, Rock N’ Roll Outdoor Live Music. Rock out for free at Hillsdale’s Outdoor Live-Music Concert Series. Bring a blanket, grab a bite to eat, beverages, cocktails or beer – picnic-style.

October 7, First Friday Nights. Swing into the weekend with music, science, animals and fun! On the first Friday of every month, from 5 pm until 8 pm, where parents and kids celebrate together at CuriOdyssey.

October 7-30  Redwood City invites you to the Zoppé Italian Family Circus. A fall tradition with acrobats, trapeze artists, high-wire acts, clowns & more.

October 8, Belmont Water Dog Run. Don’t miss Belmont’s annual Water Dog run with something for everyone, from serious runners to a Fido and kids run.

October 12, Reimagine Hillsdale Open House. Drop in at the Reimagine Hillsdale Idea Store to participate in activities and discuss your vision for the future of Hillsdale with the team.

October 14, Movie Night @ Barrett in Belmont with Hocus Pocus in the park – Friday, Oct. 14, 2022 – 6:15 p.m. – 8:45 p.m. October 15-16,

October 15, San Mateo Fall Festival. Get your fall feels from 11am to 2pm at Dr. MLK, Jr. Park in San Mateo at this pirate-themed festival with pumpkin decorating, bounce house, music, raffles, DJ music and more.

October 15-16,  Half Moon Bay Pumpkin Festival. Pumped up pumpkin mecca gears up for the 50th anniversary festival and celebration of the great and almighty gourd.

October15-16, Jim Stevens & Friends: Half Moon Bay Art & Pumpkin Festival. Don’t miss the opening act!

October 16, Annual Pumpkin Run by Senior Coastsiders. With half marathon, 10K, 5K & kids’ fun run in Half Moon Bay.

October 16, Baking Arts San Mateo Candy Class- Toffees and Brittles. In class, students will make a best-selling “butter crunch” toffee from scratch and lay both sides with dark, tempered chocolate and chopped pecans.

October 19, Bowl-o-Rama Fundraiser. Enjoy 2-hours of bowling—or cheer on your favorite teams as a spectator—enjoy pizza, beer, soda, amazing raffle prizes, all to benefit the SAMCAR Foundation.

October 21, Catch Burlingame’s ‘Ghostbusters: Afterlife’ Movie In Park. Pack blankets & movie snacks & enjoy the free show.

October 22, Central Park Celebrates 100 Years! It’s the 100th anniversary of San Mateo’s Central Park! Celebrate from 12-4pm with food, drinks, free ice cream, live music, games, and much more!  Entertainment line-up: 12:00pm – Puppet Art Theater Company, 1:00pm – National Anthem, Raising of the Flag, Presentation of the Plaque, 2:00pm – Royal Society Jazz Orchestra

October 22, Halloween Slime Creation Workshop. Join a spooky and sticky slime creation Halloween themed workshop at the Hillsdale Shopping Center and create your own personal Halloween slime.

October 22, Halloween Spooktacular. Step right up for some cool carnival games, monster maze, creepy crafts, spooky photo back drops, mini pumpkin patch, prizes & fun in Redwood City.

October 22-23 + 29 -30 Halloween Themed Kids Carnival. Aircraft checkouts, cockpit exploration, glider and helicopter construction and more are just some of the activities available in San Carlos. Catch the Haunted Hangar & Halloween Carnival: Hiller Aviation Museum.

October 27, Haunted Howl-o-ween Party for Dogs at Wag Hotels Redwood City. You and your pooch will have a spooktacular time exploring the haunted hotel, with tricks and treats around every corner!

October 28, San Carlos Halloween ‘Goblin Walk’ Trick-Or-Treat. The first 1,000 trick-or-treaters get free Goblin Walk bags.

October 29, Spooky Spokes. Get in costume, add your lights and join the Silicon Valley Bicycle Coalition for the bike parade from San Mateo’s Central Park to Bay Meadows and back. The ride is about 2.1 miles, mostly flat, and on city streets. From Central Park, you’ll ride down Laurel then 9th to Palm and turn at 25th and ride into Bay Meadows. There will be an optional loop (1.5 miles) to see the new improvements on Franklin Parkway. There will be a social hour at Fieldwork Brewing San Mateo at Bay Meadows following the ride!

October 29, Pre-register for Foster City’s SPOOKtacular Halloween Festival. Magic shows, costume contest, shaved ice and more!

October 30, Doggoween Costume Contest at Fieldwork Brewing San Mateo at Bay Meadows! Get those canines in costume and enjoy some craft brews with the neighbors. 🐶 Bring your pooch to the pup-friendly San Mateo Fieldwork taproom on Sun. 10/30 between 12pm -2pm. Winners will be announced at 2:30pm. 🏆 Top 3 winner’s humans will receive a Fieldwork gift card! We want to see your Fido as Frankenstein or a Baby Yoda or even Scooby-Doo! Be sure to tag us at @baymeadowslife #baymeadowslife too…

October 30, Halloween Witch Paddle. Join the Halloween Witch paddle in Half Moon Bay’s Princeton Harbor and don your best witch or warlock costume.

October 30, Keep Calm & Carry Yarn: Knitting Meetup. Whether you knit, crochet, cross-stitch, or any other stitching come on out and enjoy some dedicated project time at the San Mateo Main.

October 31, Harvest Festival 4-6pm, First Baptist Church invites you to the Annual Harvest Festival, All activities and events are FREE and costumes are welcome! Pony rides, Petting Zoon, Maze, Dunk Tank, and so much more!

October 31, Visit Morgan Hill for a first-time event at the pumpkin patch!  Halloween Trick-Or-Treat Candy Crawl: Spina Farms Pumpkin Patch.

Bicycle Sundays. 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.

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.