Our Picks to Show Your Local Love

From restaurants, shops, artists and more, show your love and support to our city’s creatives and visionaries. Enjoy these local establishments that you’re sure to fall for while giving back to our city’s economy simultaneously.

  1. Photo By: Ruth Shively

    Writer's Block


    WRITER’S BLOCK BOOKSTORE: Looking for a good book and quiet place to relax? Writer’s Block specializes in new releases, unique gifts and puzzles, plus events, book clubs and virtual book fairs. 316 N Park Ave, Winter Park, Florida

  2. Photo By: @CinepolisUSA

    Cinépolis Luxury Cinemas


    Dinner and a movie at Cinepolis in Hamlin. All tickets are 1/2 price on Tuesdays. Don't forget to take advantage of Happy Hour until 11 PM!

  3. Drip! Art Lounge


    DRIP! ART LOUNGE: At this “walk-in and paint” studio you simply walk in, select a canvas size and paint colors, and create a beautiful masterpiece at your leisure. 544 W Fairbanks Ave, C-1, Winter Park, Florida

  4. Photo By: The Historic Edgewater Hotel (@HistoricEdgewater)

    The Edgewater Hotel


    Spend a night at The Historic Edgewater Hotel. A modern bed & breakfast style inn that preserves the original 1926 experience in Downtown Winter Garden.



    THE LOCAL BUTCHER & MARKET: A gourmet market known for sourcing local products wherever possible, it offers meats, seafood, produce, groceries and prepared foods. 669 N Orange Ave, Winter Park, Florida

  6. Photo By: Carlos Romero

    The Vineyard


    Dinner and Wine Tasting at The Vineyard in The Grove in Windermere, where the seasonal menu changes based upon what their chef finds most fresh in the market!

  7. Original Orlando Tours

    ORIGINAL ORLANDO TOURS: Take a tour with a local native whose company specializes in Winter Park, including history and food tours. 650 N Alafaya Tr, Orlando, Florida

  8. Photo By: Jon Burket (@Jon_Burket

    Newton Park


    Catch a sunset at Newton Park, located at the shore of Lake Apopka which is known for its breathtaking views, tranquility, and abundance of small wildlife.



    HANNIBAL SQUARE HERITAGE CENTER: Established by Crealdé in 2007, the center features visual art exhibitions and education on Southern folklore. 642 W New England Ave, Winter Park, Florida

  10. Photo By: Lakeridge Winery & Vineyards (@LakeRidgeWinery)

    Lakeridge Winery & Vineyards


    Wine Tasting at Lakeridge Winery, where your personal Tour Guide will show you the winemaking area, the spectacular view of the vineyards, and guide you through tastings.

  11. POPCORN FLICKS IN THE PARK: Sponsored by the City and Enzian, this series features classic family films in Central Park on the second Thursday of each month. 150 W Morse Blvd, Winter Park, Florida

  12. Photo By: Ruth Shively

    GASP: The best gifts come in pink packages! Gasp sells fun gifts, cute trinkets, home decor and accessories for all ages, all sourced from women-owned small businesses. 106 E Canton Ave, Winter Park, FL

  13. Photo By: Ruth Shively

    KOS Coffee & Bodega: KOS is a social enterprise coffee shop and roastery that believes in creating social impact through coffee. “KOS” is short for KOSELIG, or coziness. 129 W Fairbanks Ave, Winter Park, FL

  14. Photo By: Ruth Shively

    RIFLE PAPER CO.: A stationery company whose goal is to bring beauty to the everyday, Rifle creates unique and colorfully illustrated invitations, cards, notebooks and gifts. 558 W New England Ave #150, Winter Park, FL

  15. GET UP AND GO KAYAKING: Wind through Venetian-style canals in a unique “clear” kayak and experience Winter Park’s natural beauty from the water both day and night. 410 Ollie Ave, Winter Park, FL