A perk of living in San Francisco is that wine country is a short drive away. I’m spoiled and get to wine tasting multiple times a year.
Of all the wine regions, my favorite place to go wine tasting in California is Healdsburg! This town is super cute, the locals are friendly, the vineyards in the countryside are stunning and the food scene is LIT.
Seriously, for a small town in the countryside, Healdsburg has some fantastic restaurants and bars that all are located a hop, skip and a jump away from each other.
Keep reading for my favorite downtown Healdsburg tasting rooms + restaurants and bars that are all within walking distance!
I love how the plaza is like the hub of activity in downtown Healdsburg. The plaza itself is really pretty but the fun stuff doesn’t just stop at the square. There are many side streets packed with fun tasting rooms, tasty restaurants and unique bars. You can’t get bored in Healdsburg!
My 12 Favorite Downtown Healdsburg Tasting Rooms, Restaurants + Bars That You Can Walk To
There are so many downtown Healdsburg tasting rooms, restaurants and bars that it can be overwhelming to pick where to wine taste and eat during your weekend wine trip!
These are my favorite Healdsburg restaurants, bars, and wine tasting spots all in the city and within walking distance to each other!
Boho chic meets wine country with this tasting room! Seriously – they did the tasting room experience right with comfy seating, funky decor & an all-around cool vibe. My favorite wine here is their Rose.
This is my go-to cheap food spot in the city. What I love about The Wurst is that while it’s super affordable (brats are around $8 each and large!) the food is so tasty! On a sunny day, I love grabbing a Chicken Apple brat & sitting on their colorful outdoor patio. It’s a dog-friendly!
Looking for some pretty AF craft cocktails after a day of wine tasting? Spoonbar has a tasty menu, too, but locals love heading here for Instagram-worthy cocktails that actually taste good, too.
If you like pinot noir, Cartograph makes some of the best pinot in Healdsburg! This tasting room is sleek (& a bit sciencey – you may get wine served out of a beaker!) and the whole vibe is very approachable.
On a warm day, beeline to Siduri and claim their wine seat spot so you can sip a flight or glass of wine with a fresh breeze. This tasting room offers bites, like cheese boards and sliders, to pair with your flight. Or you can purchase a glass if you know exactly what you want.
Harmon House Rooftop
On Healdsburg Ave off the square, this is the only rooftop bar in the city. It gets a bit crowded for happy hour, but if you’re craving sunset cocktails this is a great bar to visit!
Officially one of my favorite places to eat in Healdsburg! Chalkboard is Italian and they make all their pasta in-house, so come hungry & order at least one pasta dish! I love their chocolate paste (sounds strange but it’s great) Also try the fried chicken and homemade candy bar for an explosion of flavor.
A new tasting room that will be across the street from the Mill District (once that opens!) Coursey Graves’ flights have chardonnay, pinot, cabernet and syrah so it’s a crowd-pleaser wine tasting stop if you are tasting with people with different wine preferences.
This Lousiana-inspired brunch spot is always the place the girls and I visit on Sunday mornings after drinking all day Saturday. Their beignets are to die for and I always order the Shrimp and Grits (aka hangover cure!)
Duke's Spirited Cocktails
If you’re looking for the spot locals hang out on the square, it’s Duke’s. This late-night spot is always popping on weekend nights and is the most classic back bar-y bars in downtown Healdsburg. We usually stop here for one last craft cocktail at night before heading to bed. I've only been at night, but I think during the daytime it's less loud.
Williamson Wines is all about helping visitors learn about the art of pairing food and wine. They make bites in their kitchen on-site to pair with each wine you drink, with the goal of you going home feeling confident about pairing what’s in your fridge on your own!
Campo Fina is one of my favorite downtown Healdsburg restaurants! It looks like a narrow bistro from the front but they’re packing a large, open patio (complete with string lights & a bocce court) in the back! Everything on the menu is tasty but I love their wood fire pizzas to soak up all the wine after drinking all day.
The Brass Rabbit
Owned by the folks behind Chalkboard, The Brass Rabbit is a chic pasta house with a focus on seasonal ingredients (many which are sourced from the Chalk Hill Vineyard’s 4.5-acre organic farm!) They have a pasta to go box if you need to grab lunch to picnic at a winery, or come for dinner in the evening!
>>Looking for more wine tasting rooms in the Healdsburg area? Check out my mega weekend in Healdsburg guide, listing our favorite Healdsburg wineries (including my favorite nearby Dry Creek Valley, Russian river valley, Alexander Valley spots)!
Healdsburg Winery Map
A Healdsburg wineries map with all my favorite downtown Healdsburg wineries AND my favorite wineries near Healdsburg (aka outside of town, if you’re up for a short drive!) Also included all the restaurants and bars mentioned in this list!
Where To Stay In Healdsburg
There’s some really cute hotels in Healdsburg!! I love H2 Hotel, which is right off the square and has the most relaxing balconies in all the rooms. I’ts perfect for girls trips or couples. If you’re on a mega-budget, the Best Western is a spot the girls and I have totally all crashed in before to do the weekend cheap. It’s further from Downtown so you will have to Uber to dine or wine taste.
Hotel Les Mars is another fantastic Downtown Healdsburg hotel. This is a luxury hotel with sweeping ceilings, grand fireplaces to get cozy next to during winter wine tasting trips, and giant soaking tubs. Perfect for couples looking for all that romance.
I hope this helps you plan a great walking tour of Downtown Healdsburg! From cute bookstores with cats to fun local dive bars and of course, world-class artisan Healdsburg tasting rooms, there are so many fun things to do in this charming Sonoma County town.
I love Healdsburg wine tasting and spending lazy weekends drinking Healdsburg wines, eating wood fire pizzas and sipping craft cocktails. Whether it’s soaking up the summer heat or swooning over the area’s fall foliage, this wine country town is always a special place to visit.
If you have any tips to add, leave a comment below so everyone can see! Got questions? Comment or DM me on Instagram @thewhimsysoul and I’ll be happy to help!
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