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Monterey Events in May 2025: Family-Friendly Activities, Concerts, Festivals, and More
by Jill Loeffler •
Updated: December 18, 2024
My Monterey events in May calendar offers you details on the best things to do in 2025. Top picks include festivals, nightlife ideas, wine tasting activities, and so much more.
The best options this month include the California Roots Music & Arts Festival, shows at The Catalyst in Santa Cruz, and the Salinas Valley Fair.
Disclaimer: I receive a small commission from some of the links on this page.
California Roots Music & Arts Festival
Dates: 5/23 - 5/25
Location: 2004 Fairgrounds Road, Monterey
Times: 11 am to 11 pm
Price: Depending on days and level of experiences they range from $110 to $780. Children 10 and under are free with a paid adult.
Join other music lovers for this year's California Roots Music & Arts Festival. This year's top performers include Rebelution, Dirty Heads, T-Pain, Iration and more. During this three-day celebration of music and arts, you can watch more than 40 bands play every year.
California Roots tries to make sure that everyone will have an enjoyable time and they provide many different food and drink options along with the music and other activities.
Some of these include vegetarian, vegan, diary-free, and gluten-free options, so you can be sure that you and your family members will be able to eat to your heart's content. There are also craft beers and wine bars for anyone 21 and older that wants to sample some of the best of the local area's drinks.
In addition to the general admission tickets, the festival has "Redwood VIP Passes" which include extra goodies and access to special viewing areas and events.
>> Get a full schedule of this year's performers
Santa Cruz Vegfest
Dates: 5/31
Location: Boardwalk's Cocoanut Grove at 400 Beach Street in Santa Cruz
Time: 10 am to 6 pm
Price: Free
Santa Cruz Vegfest is all about celebrating everything related to living a plant-based lifestyle. This event also promotes cruelty-free and environmentally sustainable lifestyles.
You will find more than 100 exhibitors on hand with free food samples. In addition, there are numerous speakers holding discussions on animal welfare, nutrition, environment, and healthy eating habits. It's a wonderful way to learn about how to stay healthy and ways to help our planet.
Being that this is a family-friendly event, there are also lots of kids' activities throughout the day.
Tickets are free but you can reserve them in advance to save you time and trouble when you arrive.
>> Visit their site for details
Good Old Days Celebration
Dates: TBD
Location: Downtown Pacific Grove
Price: Free
The Good Old Days Celebration is one of the county's largest arts and crafts fair. It features more than 225 artists and food vendors for this weekend long event.
Not only will you be able to eat to your heart's content, but there will be great drinks on hand. Don't miss your chance to see the parade on Pine Street on Saturday morning.
On top of that, there will be loads of contests, family fun, and old-time games for all to play. If you are looking for entertainment, you will find 5 different stages with performances for both kids and adults.
The event runs from 9 am to 6 pm on Saturday, and 9 am to 5 pm on Sunday.
Salinas Valley Fair
Dates: TBD
Location: 625 Division Street, King City, CA
Times: 11 am to 10 pm
This year marks another year for this fun and family-friendly festival that features live music and carnival rides. You can also watch local animal competitions, sample local wines, and enjoy a variety of fair treats.
The theme for 2024 is “Golden Hills & Fair Time Thrills".
Some of the events that the young ones will enjoy include the Kiddie Korral, Kid's Karaoke, The Amazing Flying Carpet and the Trackless Train among others. There will also be carnival rides.
You can also experience the always competitive Miss Salinas Valley Fair contest.
Trans Am SpeedFest
Dates: 5/2 - 5/4
Location: WeatherTech Raceway Laguna Seca
Get ready to see some of the fastest and hottest looking race cars at one of the top Monterey events in May. Some of the cars driven include Mustangs, Camaros, Corvettes, Vipers, among others that will be sure to thrill as you watch them zoom by at incredible speeds.
If you are looking for some reminders of the past, there will also be a vintage racing car exhibit for you to enjoy when you need a break from the speed on the track.
Ideas on Where to Stay Around the Bay
Monterey: You will find the largest selection of hotels in and around Monterey. Higher end picks include the Spindrift Inn and Portola Hotel and Spa. You will also find some more budget friendly options if you move a few additional blocks away from the waterfront. Find my top picks for all budgets here.
Carmel-By-The-Sea: This seaside town is a bit smaller, but still offers plenty of accommodations. You will find some great luxury hotels as well as several quaint bed and breakfasts. Here are my top picks for Carmel-By-The-Sea.
Pacific Grove: This small community sits just to the north west of Monterey. They offer several great places to stay including a couple of great bed and breakfast and some budget-friendly options. Find my top 5 picks here.
Are you ready to book? Make sure to check out the great options below.
TripAdvisor: Compare prices, read recent guest reviews and find a wide selection of options.
VRBO: Another option is to rent an apartment, house, or a room around Monterey through VRBO.
Santa Lucia Highlands Sun, Wind & Wine Gala
Dates: 5/3
Location: Mer Soleil Winery at 1290 River Road in Salinas
Times: 11 am to 2:30 pm
The Santa Lucia Highlands are known for having some of the world's best Syrahs, Pinot Noirs, and Chardonnay wines in the world. This is one of the best Monterey events in May if you want to experience wine from more than 35 different member wineries.
Not only will you get to taste wine from vintners such as ROAR, Hahn, McIntyre and others, but you will also have the chance to taste some of the best small bites from restaurants in this area.
This event also features a silent auction and live music.
Did you find something you love? Make sure to pick up a bottle or two before you leave.
Tickets to Santa Lucia Highlands Sun, Wind & Wine Gala usually sell out in advance, so make sure to purchase them as early as possible for your trip. They go on sale starting February 1st. No one under the age of 21 is allowed at this event.
>> Find tickets for this fun wine and food experience
More Fun Things to Do Around Monterey Bay
Monterey Bay Aquarium: One of the best aquariums in the world is right here in the Monterey Bay. It's a must see on your stay. The aquarium is home to more than 500 species of Monterey Bay plants and animals.
Whale Watching: May is a fun time to head out on the water to try and spot migrating whales in the area. This time of year, you will get the chance to see humpback and blue whales as well as dozens of other sea animals. Trips leave daily from Monterey. Find tickets for all dates in May.
Food Walk: Sample local foods and learn all about the area on this fun Monterey Food Walk. You will sample both savory and sweet treats as you walk from place to place. In addition, you will also get the chance to pair some of your tastings with our top local wines and craft brews. All food is included in the ticket price. Pick up your spot on the tour today.
Shows at the Golden State Theatre
Check out some of the best Monterey events in May at the Golden State Theatre. Here are their top shows this month.
Carmel Valley Garden Show
Dates: TBD
Location: Hidden Valley Music Seminars at 104 W. Carmel Valley Road in Carmel Valley
Times: 10 am to 4 pm
Price: Free; Parking $1
The Carmel Valley Garden Show is one of the Monterey events in May that has so much more than you could imagine from the name of it. Stop by to admire the professionally judged Plant and Flower exhibitions. Your kids will also enjoy the Children's Garden and many other activities specifically for them.
In addition to the flower exhibits, there is a photography contest, a silent auction, and a Garden Gala where the most outstanding arrangements are assembled. There are large number of vendors in case you want to outfit your own nursery or garden with some of the best plants and flowers anywhere.
There will also be music, food, and drinks available at the Garden Cafe.
Carmel Art Festival
Dates: 5/16 - 5/18
Location: Devendorf Park in Carmel-by-the-Sea
Price: Free
This event gives you the chance to see some of the best local artistry in the gorgeous village of Carmel-by-the-Sea.
This festival is the only one of the Monterey events in May that has 60 artists. Each one will be showing their talents as they paint during the exhibition live and in person. This offers you the chance to get a behind the scenes look at how they produce their artwork.
There will also be talks, live music, sculpture-in-the-park exhibits, and much more.
The artists will be competing for awards as they paint their pieces and show them at the different galleries around the area. One of the fun things to do here is vote on the painting you like the best and see if it wins the "People's Choice" award!
Last but not least, there is a Kids-Make-Art section so your little ones can experience what it is like to learn about and make their own pieces of art during the day.
Posters, hats, t-shirts and paintings are available for purchase. Paintings that aren't sold during the show will be offered at a "Buy Now" price at the end of the weekend.
More Events Nearby
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