Explore Pet-Friendly Outdoor Activities in Winter Haven, FL

Posted: March 16, 2023 | Categories: Communities>Chestnut Creek | Pet Friendly Homes & Communities | Communities>VillaMar
By Sunny

Updated December 26, 2023

Sunny Highland Terrier on Lawn

Are you searching for a new home in Winter Haven, Florida, that’s perfect for you and your furry friend, and wondering what there is to do together around town? It’s Sunny, the Highland Homes pup, and boy, do I have the scoop on some paws-itively fabulous pet-friendly activities in Winter Haven! 

Spots to Sniff Out

Winter Haven, Florida, is heaven for those of us with wagging tails with dog-friendly parks, restaurants, and activities – the opportunities to have a ball are endless. Living in Winter Haven also means my best friend and I can spend the day out on the water or waterside, with 50 lakes in the city including 19 interconnected lakes that make up the Chain of Lakes.

Living the Chain Life

Dog on a boat on the Chain of Lakes Winter Haven Florida
One of my pup-pals living the Chain Life


Known as the “Chain of Lakes City,” Winter Haven has plenty of my favorite thing – water! If you’re moving to Winter Haven from elsewhere, you might be wondering what I am talking about. The Chain of Lakes is a famous series of lakes connected by canals and locks. This means you can boat from lake to lake and travel from one side of the city to the other, all without leaving the water! And, many lakeside restaurants and pubs have docks where you can tie up and stop for a bite or beverage. Pretty cool, right!?

My favorite water activities on the Chain of Lakes are chilling on the boat, laying on the front of the kayak with the breeze in my face, or hanging on a paddleboard with my favorite human. I especially like when we go through the lock between Lake Shipp and Lake Lulu and cruise past Harborside (it’s one of my favorite restaurants; I’ll tell you more about it later) because all the humans sitting outside tell me how cute I am in my special boat vest.

Sometimes my human spends time on the water without me, going jet skiing, tubing, or water skiing. It’s cool because those aren’t my favorite activities, so I just hang out at home or sometimes with a human friend at the park or beach.

I could woof about the water ALL day but I have SO many other things to talk about, so here are some links to learn more about the Chain Life and all of our lakes in Winter Haven.

Dog-Friendly Parks and Trails

Auburndale's TECO Trail

Whether the order of the day is to relax under a shady tree, pack a dog-friendly picnic, or take a walk, Winter Haven is home to dog-approved parks and recreation:

  • Simmers-Young Dog Park in Winter Haven, FL
    Simmers-Young Dog Park
    The K9 Courtyard is my favorite place to run around in Downtown Winter Haven. Located off the Chain of Lakes Trail, it's nice and shady and designed for pups like me to run and play off-leash.
  • Simmers-Young Park (and Dog Park) is my go-to on the west side of Winter Haven, with an off-leash dog park with separate spaces for large and small dogs and some fun ramps and stuff to play on. Leashes are required outside of the dog park, where there is a playground, sports fields, picnic areas, and much more!
  • When I want to take a picnic or sit in the shade, Lake Shipp Park offers pup-approved green space with lots of trees and great views on the shores of Lake Shipp. It also has a playground, boating, and fishing opportunities.
  • Another great, pet-friendly spot, South Lake Howard Nature Park is my go-to Winter Haven nature trail where I can go for a walk and see beautiful greenery and animals like squirrels! My human says it’s really peaceful because it’s on the lake and has boardwalks and fishing piers, plus a lot of trees, and enclosed picnic areas where we can sit together and relax and sometimes eat lots and lots of treats.
  • Just outside of Winter Haven, you’ll find two of my other favorite dog parks – Lake Crago Dog Park in Lakeland and Auburndale Dog Park in Auburndale, located right off the Auburndale TECO Trail which is also one of my favorite places to go for a long, shaded walk!

Bone Appetit!

Harborside Restaurant in Winter Haven
The waterside patio at Harborside


Don’t mind me! I’m drooling at the thought of all the scrumptious bites to sneak from my best pal’s plate. If you thought the list of places to run wild was as good as it could get, wait! Winter Haven is also home to an array of mouth (or snout!) watering spots to grab a bite to eat. While Florida law dictates all animals must remain outside at restaurant establishments, Winter Haven is home to many dog-friendly restaurant and pub patios:

  • Harborside, Winter Haven's popular waterside restaurant (and my favorite restaurant), serves a variety of seafood, pasta, steaks, and more. 
  • The Twisted Prop Bar & Grille, a local favorite delivering American classics on a dockside patio on Lake May.
  • Tanners Lakeside serves up classic, appetizing American choices with a pet-friendly outdoor tiki right on the waters of Lake Howard.
  • Dino’s Drive-In is an old-fashioned drive-in where you can enjoy classic American selections.
  • Lucille’s American Café has been serving up comfort food in Winter Haven since 1999, with a casual atmosphere.
  • Old Man Frank’s serves up classic pub fare on a lakefront deck. 
  • At The Union Taproom, the promise of delicious pizza and a self-pour wall with more than 40 beer, wine, cold brew coffee, ciders, and kombucha taps keep people (and pups) returning for more!
  • Grove Roots Brewing Company is downtown Winter Haven's local craft brewery and taproom, and the large outdoor patio and Biergarten have picnic tables, lawn chairs, grass, and lawn games. It's the bee's knees for relaxing with friends!
Grove Roots Brewing Company in Winter Haven
Courtesy of the Winter Haven Chamber of Commerce


A local gem that can’t be missed, the Winter Haven Farmers Market is the place to be every Saturday! Open from 9 a.m. to 1 p.m., rain or shine, this pet-friendly market is a fantastic location to stock up on fresh fruits and veggies, craft goods, baked treats, plants, and additional locally-made treats. The market is located across from Grove Roots Brewery on the Northeast corner of 3rd Street and Avenue C SW in downtown Winter Haven.

Looking for more? Check out Bring Fido for additional dog-friendly restaurants in Winter Haven!

Pet-Friendly New Homes in Winter Haven, Florida

Interior of a new home in Winter Haven, FL at Chestnut Creek

Winter Haven, Florida, is one of my favorite places in Central Florida for pet-friendly outdoor activities! If you are looking to find a fur-ever home for you and your furry friend, we build in two Sunny-approved neighborhoods of new homes in Winter Haven located near all of these amazing dog-friendly activities.

Our team at VillaMar is ready to roll out the red carpet for you and your best pal with new homes priced from the $270's offering 1,301 to 2,029 square feet of living space with three or four bedrooms, two to three-and-a-half bathrooms, and flexible plan options to suit your needs. Making the most of Winter Haven’s natural assets, homes here are situated amongst open space, ponds, and wetlands, adjacent to the shores of Crystal Lake, and VillaMar also offers amenities including a pool and playground on the lake shores.

Over at Chestnut Creek, my furry friends are living the life in spacious 1,819 to 2,956 square foot homes priced from the $330’s, with a big backyard to play in thanks to the ¼-acre homesites. These beautiful, pet-friendly homes include three to five bedrooms, two to three-and-a-half bathrooms, and a two or three-car garage, and are tucked away in a country-like setting just south of Lake Fannie.

Lanai on a Florida new home
See that sofa? It's my fave spot to stretch out on the lanai.


Part of what makes these new homes in Winter Haven pet-friendly are the design options available. When you build with Highland Homes, a professional designer will help you choose the features and finishes for every room in your new home! Some of the home design options that pet parents love are:

  • Durable, easy-to-clean flooring such as luxury vinyl plank, ceramic tile, and laminate.
  • Drop zones, providing optimal space for pet dishes or a litter box.
  • Tiled walk-in showers and utility sinks for bath time.
  • A screen-enclosed lanai, providing secure outdoor living space for you and your pets.

Ready for your VIP-P (Very Important Pet-Parent) tour? Click the Call or Email buttons on the screen to connect to learn more about our new homes in Winter Haven or other Highland Homes’ Florida communities near you.  

Tags: Pets Dog Park Walking Trails Winter Haven Relocating to Florida Chain of Lakes VillaMar Chestnut Creek