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7 Fall Date Ideas in Pittsburgh

October 27, 2021

The fall season is lovely, with the leaves changing and the temperature cooling down. The dating ideas in Pittsburgh will change from enjoying the heat of summer to taking in the fall activities that the city has to offer. Dive into these seven ideas for your next date in this fall season.

7 Fall Ideas for Dating in Pittsburgh

         1. Dinner at Le Poulet Bleu

A plate of food

Le Poulet Bleu is a French-inspired American bistro voted Best New Restaurant of 2018 by Pittsburgh Magazine. This restaurant is the perfect place to take your date in Pittsburgh during the fall season as the ambiance and menu are incredible. You and your date can share a few appetizers and then finish the night off with a dessert paired with a special wine.

       2. Visit the Threadbare Cider House & Meadery 

A bottle of wine and a plate of food

Fall calls for pumpkin spice and apple cider, which is why the Threadbare Cider House & Meadery is an excellent place for a date. This location was named after Johnny Appleseed, who walked through Pittsburgh from Massachusetts in his threadbare clothing. The family-owned cider house uses regional apples to ensure that each cider is deliciously produced. It is tucked behind a historic tannery with a farmhouse charm that pairs well with the drinks they offer. The Threadbare Cider House & Meadery also includes lunch, dinner, and brunch options to pair with your ciders. 

        3. Explore the Van Gogh Exhibit 

person sitting on the ground at the Van Gough Exhibit in Pittsburgh

Change up your date night with the immersive Van Gogh Exhibit. With 500,000 cubic feet of projections, this is something you both won’t be able to take your eyes off of — and it’s a creative conversation starter. These experiences are held worldwide, with each one tweaked to highlight the architecture of its building. Once you step inside, you’ll be transported to an entirely new reality that encourages you to take in art in a new way. 

        4. Discover the new Bakery Square in Pittsburgh

Bakery Square at night

Bakery Square was once the home of Nabisco Bakery, but it has now transformed into office spaces, shopping centers, and restaurants. Bakery Square is a contemporary area where you and your date can grab a bite to eat, check out a few shops, and end the night with a drink. You don’t have to sit at the same bar or restaurant all night — this is a fantastic place to continue the date elsewhere. If you and your date are interested in sports, a big screen broadcasts Pitt, Pens, and Steelers games throughout the seasons.

         5. Enjoy Fall Foliage at Narcisi Winery

Bottles of wine in a park with pumpkins

Narcisi Winery is a family-owned winery located just outside of Pittsburgh in Gibsonia, PA. Because it’s outside of the hustle and bustle of the city, there are more trees and landscapes to appreciate the colors of the changing seasons. What started as a cellar in a home in Coraopolis soon turned into the winery and restaurant they have today. The winery offers classic wines for those who want to stick with what they like and unique wines for those who love to try something new. You and your date can take a seat at the restaurant or venture through a private tasting. 

       6. Listen to Jazz at Con Alma

inside the Con Alma bar

Grab a few cocktails and relax to the sounds of jazz with your date at Con Alma. This restaurant embraces the rich history of jazz and strives to return this genre of music to the forefront of the local music scene. Con Alma showcases local jazz musicians seven nights a week, including their Latin Jazz Sundays. Their menu is Latin-inspired with foods from countries such as South America, the Caribbean, and Mexico. The cocktails are prohibition-inspired, and there are wine lists with options from all over the world. 

       7. Take a Weekend Getaway to Nemacolin

The Nemacolin at night

If you are searching for the perfect weekend get-a-way, take your date to Nemacolin. This luxury resort offers various options for places to stay and things to do. The Falling Rock Hotel at Nemacolin is a bespoke oasis that includes art deco interiors, luxury amenities, and even butler service. Nemacolin also offers wildlife adventures, Jeep off-roading, luxurious spa experiences, theater performances, fine dining restaurants, and more. 


There are so many things to experience while dating in Pittsburgh, especially during the fall season. The Modern Matchmaker ensures that you are spending quality time with meaningful and compatible matches. Contact us today to begin your journey to finding your perfect match.

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