Weekend Getaways Historic Downtown Sanford

Promoting Weekend Getaways in Historic Downtown Sanford

Historic Downtown Sanford is too good to keep a secret. Recently we hosted a team of Instagrammers and bloggers from Orlando and Tampa to show them what a weekend getaway in Historic Downtown Sanford may look like. Many stayed in the beautiful bed & breakfast The Higgins House.

Higgins House Bed and Breakfast

First Stop: The District

This is the happiest happy hour I’ve ever been too. I sip their Bobandy cocktail which is a smooth mix of gin, lemonade, cucumber, and mint. I also get to sample their zingy jalapeno margarita.

We’re set up in front of the restaurant with a perfect view of Palate Coffee Brewery’s open-mic night across the street as well as Pedal Driven Co.’s bike-a-thon that streams down the road. Our table is long and narrow, like the Last Supper, and we all share platters.

The Australian Wagyu Tri-Tip: served with Shishito pepper polenta and an heirloom carrots micro-salad.

Bourbon Bone-In Pork Chop: topped with a thick, sweet fig sauce.

We fill up, expressing how we won’t have room to eat more. Of course, that won’t stop us.

Second Stop: Celery City Craft

The pub is abuzz with Porchfest pre-partiers. The kitchen has opened its doors to Rice & Spice, a Thai street food pop-up, and the stage is set with Run Raquel, a female-fronted band covering classics such as ‘Valerie’ and ‘Fell in Love with a Girl.’

Our feet crunch over red gravel as we head to get craft beer, spring rolls, and curry. We settle down at a picnic table and slurp down our drinks to counteract the spicy rice.

Third Stop: The Old Jailhouse

Sanford’s newest, most anticipated restaurant has a history dating back to 1890 when it first served the community as a blacksmith and wagon shop. Now, the dining experience echoes its Seminole County Jail days (ca. 1914-1959) with bars in the windows and jail cells doubling as seating areas.

With intermittent sips of champagne to cleanse the palate, we feast the Old Jailhouse’s renowned sunbelt cuisine.

Creole Lamb Shank: topped with a spicy bell pepper sauce.

Braised Pork Belly: balanced on buttermilk cornbread and topped with tomato chutney and pickle.

Portobello Sandwich: spiced up with pine-nut caponata and chipotle aioli on a potato roll.

Shrimp Skewer: dripping with gravy and hovering over hot collard greens and cheese grits.

For dessert, we rotate three plates:

Red Velvet Shortcake: frosted with pink-speckled icing and situated on a bed of caramelized pecans.

Pecan Brownie: crisscrossed with dark and white chocolate sauce.

Banana Pudding: crunchy on the outside, doughy on the inside, and warm all the way through.

Final Stop: Wolfgang’s Dessert Room and Speakeasy

We arrive for a nightcap at Luisa’s Cellar. After asking the bartender for the password, we head upstairs en route to the hidden speakeasy. Along the way, we pass through their second-floor bookstore, stocked with everything from board games to Manga series. There’s also a table where wine tastings and classes take place.

One of us calls the password through a door in the corner. We are admitted inside. The speakeasy is a smaller, intimate room furnished with deep red tablecloth, lamplight, and an electric fireplace.

I sip a vermouth cocktail and smile at our visitors marveling over the speakeasy. To me, it’s my weekly Friday spot. To them, it’s a whole new adventure.

Saturday: Porchfest

There’s always something going on in the weekend. This particular Saturday, Sanfordites are being spoiled with the Sanford Porchfest Music Festival. Forty-four bands and artists jam out on ten front porches within the historic residential district. You can pack a picnic, walk or bike around, and meet new neighbors as live music floods the red-brick streets.

The best part is, all of the festival’s proceeds—collected through sponsorships, donations, and merchandise sales—are donated to scholarship programs and performing art summer camps for underprivileged children.

I get to hear Run Raquel again while lounging on a sofa in someone’s front lawn. It occurs to me that not many music festivals are like this. And not many towns are like Sanford.

Pick any weekend in Historic Downtown Sanford and the festivities will rival any other weekend getaway. The team at HistoricDowntownSanford.com intends to make that known. We look forward to inviting more bloggers and Instagrammers from other areas of Central Florida so they too can enjoy and tell the tales of our great downtown.

Rachel Sammons

Rachel slings lattes at Palate Coffee Brewery, pens the arts column for the Sanford Herald, and eats a lot of Pocky. When in Sanford, she likes to sing that line from "It's Time" by Imagine Dragons that goes, "I don't ever want to leave this town!"

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