California's 'Jewel Of The Hills' Is A Dreamy, Walkable City With Perfect Weather Just Outside San Diego

Southern California's nearly perfect year-round weather attracts visitors worldwide to explore its picturesque destinations. In particular, the San Diego region is a bucket list city for many as home to one of the best Little Italys in America and historical sites such as Old Town, a history lover's paradise and California's oldest city. Not far outside America's Finest City limits, lies the dreamy, walkable city of La Mesa, known as "The Jewel of the Hills," and a worthy travel stop for those venturing into the region.

La Mesa, with a population of approximately 60,000, adopted its nickname because of its location in the heart of the rolling hills outside of San Diego, while taking its actual name, which translates to "the plateau," from its surrounding geography. There are several mountains in the area, including the 1,593-foot Cowles Mountain, the tallest point in San Diego; the North and South Fortuna Mountains; and 1,300-foot Mount Helix. Known originally as La Mesa Springs, it became a railroad stop for the San Diego and Cuyamaca Eastern Railway with the building of the historic La Mesa Depot in 1894. The name was eventually abbreviated, and the city was officially founded in 1912. It also includes a role in movie history, as a studio filmed approximately 150 silent movies there in the early 1900s before moving operations to Santa Barbara.  

Across La Mesa's 9 square miles, you'll find history, art, local shops, and dining options, away from the busy tourist attractions most flock to in San Diego. Many are drawn to its cute downtown area on La Mesa Blvd., which is known as "The Village." The Village hosts the largest Oktoberfest in the San Diego metropolitan area, drawing 100,000 visitors annually, along with other community events. 

Strolling through the Village means starting your day at Swami's Cafe for breakfast or lunch from the extensive food and beverage menu. Then hunt for a bargain or specialty item inside the La Mesa Antique Mall or Bohemian House Vintage antique stores. Check out the Walkway of the Stars, where local La Mesa volunteers are honored, and visitors can enjoy a series of murals highlighting town events and activities.

History buffs will want to head to the La Mesa Depot Museum, the town's oldest building, where a steam locomotive and freight cars are on display, along with exhibits in the former baggage room. Tours are available Tuesdays and Thursdays from noon to 3 p.m. and Saturdays from 11 a.m. to 2 p.m., but you can view the displays at any time. For more history, visit the La Mesa History Center inside the historic McKinney House & Museum, open Saturdays from 1 p.m. to 4 p.m. There's also a list of historical landmarks available with addresses on the town's website.

La Mesa created three urban trail walking routes through the city, each of varying lengths and ability levels. You can find maps and descriptions of the 1-mile beginner "Stroll," the 5-mile intermediate "Stride," and the 3.5-mile advanced "Challenge" route on the website. You can also take on the Secret Stairs in the Mt. Nebo/Windsor Hills neighborhood, with a website map depicting the three steep public stair routes for a challenging workout. Head back to the Village afterward, where you can grab a pint and pub favorites at the The Hills Pub or a slice or two at Surf Rider Pizza.

La Mesa is located 20 minutes from the San Diego International Airport, where a bus to downtown can connect you to the San Diego Trolley lines, serving several La Mesa stops. Take the Orange line and depart at the La Mesa Blvd. stop, and you're in the walkable downtown, ready to explore. If you're using Amtrak's Pacific Surfliner to arrive in San Diego, you can connect to the Trolley and bus lines at both the Old Town and Santa Fe Depot stops.

You'll want a car or to call a rideshare to visit two of La Mesa's outdoor gems, Mt. Helix Park and Lake Murray Reservoir. Mt. Helix Park, known as the "Crown Jewel of East County," features a historic amphitheater, the easy Yawkey trail, and 360-degree views from the mountaintop. Lake Murray is part of the expansive Mission Trails Regional Park, with a 3.2-mile loop trail, watercraft rentals and access, and picnicking. Both spots are ideal for catching a sunrise or sunset, and generally open between those hours. There's no bad time of year to visit, as the weather is picture-perfect nearly every day. Summer months will feature slightly hotter temps than most of coastal San Diego, given La Mesa's inland location.

Several chain motels have properties in La Mesa, including a Best Western, Holiday Inn Express, and Days Inn and Suites. There are options within walking distance to the Village on Airbnb and VRBO, and camping and RV choices in the greater San Diego area, not far from La Mesa. You can also opt to book a room at the Lafayette Hotel, an iconic historic landmark voted one of America's best hotels in 2024, about 17 minutes from La Mesa.