Similar to its shopping scene, Winter Gardens itself is rather bereft of neighborhood parks. However, several parks can be found in adjacent neighborhoods to suit your needs just a short drive away.
Santee Lakes features an array of activities, such as paddle-boating, picnicking, fishing and camping. Prices for each activity vary, but parking can be had at a daily per-vehicle rate and generally goes for under $10, even for attendance to special events. The lake water's blue clarity will draw you in, and the lovely landscape will keep you in thrall. Visit Santee Lakes with friends or family to see for yourself why locals love to come here to get away from the daily grind.
Shadow Hill Park on Shadow Hill Road gears itself toward the family crowd. Featuring two playgrounds specifically designed to be age-appropriate for all youngsters — a "big kid" and "little kid" area — and an expanse of grassy flat land that's perfect for picnicking, Shadow Hill Park's amenities make it a fun place for a family to spend the day. Parking costs nothing, and plenty of it is always available. Head over to Shadow Hill Park with the kids for a great day of playing and laughing.
Winter Gardens does not have a reputation as a haven for shoppers. However, even though the neighborhood lacks boutiques and speciality shops, you can still find the basics within the boundaries of the town. The Albertsons on Winter Gardens Boulevard has a huge stock of every grocery item you could ask for while Parkway Plaza in nearby El Cajon can fill all of your mall-shopping needs. East County Square, located just across the Interstate 8 from the Winter Gardens neighborhood, features several chain stores.
Cost of living in Winter Gardens compares favorably with the city of San Diego. Gas prices here may be around 4 percent higher than the average for the United States, but they are 3 percent lower than the average for California. When it comes to housing, Winter Gardens wins. A one-bedroom
apartment rents around $1,100 per month as compared with San Diego's average of $1,300 per month. Entertainment prices reflect the lower cost of living in Winter Gardens. The average beer at a pub or bar will run about $3, perhaps even less if you take advantage of specials.
Getting around in Winter Gardens can be a challenge for pedestrians, as some of the roads within the neighborhood do not have sidewalks. Despite this lack of walkability, there are several bike routes set up in the area to cater to cycling enthusiasts. Two buses serve the region for people who prefer to use public transportation to commute, though the schedules of these buses are limited, making them amenable to daytime commuters and few others.
Calling ahead for a taxi or an Uber remains an option if driving does not seem feasible, though most who live here opt to drive in order to get around. Street parking can often be found easily, and paid parking is unheard of in Winter Gardens. These factors, paired with easy access to two freeways, make Winter Gardens a good place to live for people who like to drive.
Originally part of El Cajon and Lakeside, Winter Gardens shares the same history as the towns that now surround it: a place for wealthy San Diego denizens looking to get away from it all in the countryside, as well as a great stopping point between Julian and the port of San Diego during the California Gold Rush.
Winter Gardens does not feature any noteworthy annual events, nor is it home to any museums or art galleries. However, the neighborhood has such attractions nearby. A few miles away in Lakeside on Maine Avenue, you can find the Lakeside Rodeo, featuring live events at regular intervals throughout the year performed in the rodeo tradition. Down in neighboring El Cajon tucked away on Rea Street, art enthusiasts can visit the Olaf Wieghorst Museum, dedicated exclusively to the life and works of the eponymous Danish painter.
Many of the eateries in town are found along Winter Gardens Boulevard, the neighborhood's main strip. While other restaurants scatter along Highway 67 to the north and Interstate 8 to the south.
If you feel the need to sink your teeth into a hearty, hand-crafted sandwich, head over to The Grinder for a signature foot-long Italian sub. The Grinder offers sandwiches such as the Godfather, which contains piles of pastrami, salami, ham, roast beef, Italian sausage and meatballs. Order sandwiches by half for a lower price, so if you find the foot-long too daunting, you can always get a 6-inch instead. Carb watchers can order any sandwich in a bowl rather than on a bun.
For a slice of pizza served up in a casual environment that doesn't put on airs, stop by Hole in the Wall Pizza Shoppe on Winter Gardens Boulevard. The name pretty much describes the vibe of the place. Locals love Hole in the Wall for its signature Philly cheese steak pizza topped with slices of juicy steak, onions, peppers and lots of gooey cheese. Owners started the business in 1977, and the friendly small-town service keeps their doors open year after year.
Greek Chicken features traditional Greek cuisine with American favorites. Locals love the onion rings, while regulars rave about huge portions that arrive at your table. Although sides, sandwiches and salads proliferate the menu, start out with just one item and go from there. The fresh baklava contains plenty of taste in between layers of flaky phyllo dough.
After the sun sets, make your way over to the Coo-Coo Club on the corner of Winter Gardens Boulevard and Orchard Road for an unforgettable dive bar experience. The Coo-Coo Club lives up to its name when karaoke and theme nights, such as dress in your PJs night, combine with plenty of beers on tap. PJ night means wearing bedtime attire gets you drink discounts. This little hole-in-the-wall keeps you entertained without hitting the jukebox.
For live music after dark, check out The Study Lounge on Greenfield Drive. The joint features local music acts and drink specials, while the atmosphere makes it easy to tip back a glass and nod your head as you rock to some garage-band tunes.