A Complete Guide to Visiting Tailwind Tavern

Nestled in the heart of downtown Arborvale, Tailwind Tavern has carved out a name for itself as one of the area’s most beloved gathering spots. Whether you’re a seasoned local or a curious newcomer, visiting this rustic-chic establishment is more than just grabbing a quick bite—it’s an experience rich with ambiance, flavor, and community spirit.

TLDR (Too Long; Didn’t Read)

Tailwind Tavern is a charming gastropub offering locally sourced dishes, expertly crafted cocktails, and a warm, welcoming atmosphere. Conveniently located in Arborvale, it features weekly live music, a rotating craft beer selection, and rustic interiors perfect for both casual and special occasions. For the best experience, book ahead on weekends and explore the seasonal menu. Don’t miss their signature Tailwind Burger and house-infused whiskey flights!

About the Tailwind Tavern Experience

Tailwind Tavern isn’t just a place to eat—it’s a destination where community and craftsmanship shine. With its exposed brick walls, reclaimed wood furnishings, and custom aviation-themed décor, the tavern is as visually inviting as it is palatable. Everything about the visit—from the moment guests walk in to the final dessert bite—exudes thoughtfulness and authenticity.

Why Locals Love It

  • Signature Dishes: Highlights include the Tailwind Burger topped with candied bacon and chipotle aioli, and the trout filet freshly caught from nearby lakes.
  • Zero-Waste Philosophy: The tavern uses upcycled materials and composts all kitchen waste, making sustainability a priority.
  • Live Entertainment: Weekly features include local bands, traveling folk duos, and open mic poetry nights.

Menus and Specialties

The kitchen at Tailwind Tavern rotates its menu seasonally to showcase fresh, local ingredients. Meat-lovers, vegetarians, and gluten-free diners alike will find something to love. Standout items include:

  • Tailwind Burger: 8 oz. locally-sourced beef, candied bacon, homemade pickles, chipotle aioli, brioche bun.
  • Grilled Portobello Tower: Layered mushrooms, goat cheese, sun-dried tomato puree, and arugula salad.
  • Smoked Trout Board: Cold smoked with alderwood, served with charred flatbread, pickled onions, and zesty horseradish sauce.

For the sweet tooth, the Salted Caramel Pot de Crème is a must-try, while those looking to sip something special should check out the house-infused whiskey flights.

Drinks and Craft Beverages

The bar program at Tailwind Tavern is as robust as its kitchen offerings. From small-batch bourbons to local IPAs, every beverage is hand-selected or handcrafted to complement the food and atmosphere. Highlights on the drink list include:

  • Seasonal Craft Cocktails: Rotating selections like a maple old fashioned or lavender gin fizz.
  • Local Brews: On tap you’ll find Arborvale Stout, Red Pines IPA, and seasonal farm ales.
  • Mocktails: Non-alcoholic options like the Ginger Orchard (ginger beer, apple shrub, lemon) cater to all palates.

Happy Hour Highlights

Happy Hour runs weekdays from 4–6 PM and includes discounted starters, $6 wines, and half-off draft beers. It’s a local favorite and generally fills up quickly—early arrival is recommended!

Atmosphere and Interior Design

Inside, the tavern offers a blend of industrial and rustic design. Edison bulb lighting casts a warm glow over natural wood and metal fixtures, while vintage aviation memorabilia—nods to early air travel—adorn the walls. Several cozy booths and a communal wooden table create an inviting vibe, whether you’re flying solo or out with friends.

Events and Live Entertainment

More than just a dining destination, Tailwind Tavern serves as a cultural hub. Their weekly lineup includes:

  • Thursday Trivia Nights: Hosted by local personalities with drink prizes and giveaways.
  • Friday Live Music: Featuring indie, bluegrass, and classic rock performers from around the region.
  • Sunday Brunch Jazz: Calm and classy tunes accompany a specialty brunch menu including mimosas and seasonal quiche.

Events are often posted on the tavern’s social media accounts and website, so checking ahead ensures guests don’t miss out.

When to Visit

Tailwind Tavern is open Monday through Sunday, 11:30 AM – 11:00 PM. Brunch is served on weekends from 10:00 AM to 2:00 PM. The busiest hours tend to be Friday and Saturday nights, especially during special events or holidays, so reservations are highly encouraged.

Best Times for Different Experiences

  • Romantic Dinner: Try weeknights after 7:30 PM for a quieter, candle-lit ambiance.
  • Family Meals: Weekday lunches and early Sunday brunch are perfect for families with children.
  • Night Out: Arrive by 6 PM Friday for the best chance at finding seating before live music begins.

Location and Parking

Located at 52 Windmere Avenue, Arborvale, Tailwind Tavern is easily walkable from most downtown hotels. Ample free street parking is available on Windmere Avenue and surrounding streets. For those taking public transit, the #7 Arborvale Loop Bus stops right across the street.

Tips for First-Time Visitors

  • Reservations: Available online or by phone, recommended for Friday and Saturday nights.
  • Dietary Accommodations: Gluten-free, vegetarian, and vegan options are clearly marked on the menu.
  • Pace Yourself: Portions are generous—consider splitting an appetizer or dessert.
  • Check the Board: Their specials board often features off-menu items worth trying.

Final Thoughts

With its carefully curated menu, artistic atmosphere, and warm community feel, Tailwind Tavern sets the bar high for neighborhood gastropubs. Whether making it a regular haunt or marking it as a must-visit on a weekend getaway, guests walk away with more than just a full stomach—they take home a memory. Don’t forget to snap a picture beneath the iconic “Fly With Flavor” mural near the patio!


Frequently Asked Questions (FAQ)

Do I need a reservation to dine at Tailwind Tavern?

Not always, but it’s recommended on busy nights. Fridays, Saturdays, and event nights tend to book quickly, so a reservation ensures the best experience.

Are kids welcome?

Absolutely. Tailwind Tavern is family-friendly and even offers a kids’ menu with smaller portions and mild flavors.

Is there outdoor seating?

Yes, weather permitting. Their patio area is open late spring through early fall and includes heaters for cooler evenings.

Does the tavern accommodate dietary restrictions?

Yes. They provide clear menu labels and can prepare most dishes to fit common dietary needs including gluten-free, vegetarian, and vegan standards.

What kind of music is played live?

Live music ranges from acoustic singer-songwriters and jazz trios to full band indie rock and folk. The selection changes weekly and showcases local talent.

Can I host a private event at Tailwind Tavern?

Yes, the tavern offers private dining options and event rentals for groups of 10–50 people. Contact their event coordinator for personalized menus and pricing.