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Staycation: How to Spend a Magical Weekend in Medina This Time of Year

City Guide, Getaway, Things to Do, Where To Stay

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Written by Jessica Kelly

Published on November 22, 2022

This guide was originally written and published in 2018 and has been updated. Some dishes and products may have changed since.


A huge thank you to Scott, Alix, and the rest of the team at the Shirt Factory and the beautiful Hart Hotel for having us!

Medina Road Trip / Photo x Jessica Kelly

Just under an hour outside of Buffalo is the perfect location for a cozy overnight getaway during the holiday season. The Village of Medina has plenty of cute shops, bakeries, and bars as well as long standing traditions for locals including the very popular Olde Tyme Christmas celebration which has been said to resemble “It’s a wonderful life”!


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Each year during the Olde Tyme Christmas Festival, they celebrate the kickoff to Christmas with a fireworks show, street vendors, and a parade of lights. The surrounding bars blast Christmas music while hosting after parties and create special pop up cocktails for the season. Although this event only happens annually after Thanksgiving, the holiday themed cocktails live on throughout the season for locals and visitors to enjoy. It’s the perfect excuse to plan a visit and explore the area.

Medina Road Trip / Photo x Jessica Kelly
Medina Road Trip / Photo x Jessica Kelly

After just a short time in the village, you’ll begin to notice just how encouraging the community is. Everyone seems to know everyone and local businesses don’t compete, they support each other the way neighbors should! If you are planning a visit, Here’s how to spend an overnight staycation/getaway in Medina:

Day 1


Checking in at Hart House Hotel

113 W Center St, Medina, NY 14103 / harthousehotel.com

The Hart House Hotel dates back to 1876 when the building was packed with 30 rooms to cater to the bustling Erie Canal stop point. The cozy hotel in Medina even has a connection to the Thousand Islands! The proprietor, Elizur Kirke Hart, decided to build a modest summer home filled with 80 rooms on an island. After he passed away, the island remained named after him (although, with the proper spelling of ‘heart’), but the cottage was torn apart and turned into the now famous Boldt Castle built for George C. Boldt on the St. Lawrence River.

Hart House Hotel / Photo x Jessica Kelly

During our visit (2018) we stayed in the 400 square ft MicroLoft on the 3rd floor with a comfy queen bed, high ceilings, exposed brick and rafters, and the original vintage paint that’s been preserved on the walls. The fireplace was lit when we arrived, making the room so warm and welcoming. There’s an espresso bar, plenty of channels to flip through before bed on the TV, and even a gym (you know, if that’s your thing) to workout in on the grounds just to name a few of the great amenities. Best of all, they’re just around the corner from the strip with shops and restaurants to explore!

Hart House Hotel / Photo x Jessica Kelly
Hart House Hotel / Photo x Jessica Kelly
Hart House Hotel / Photo x Jessica Kelly
Hart House Hotel / Photo x Jessica Kelly
Hart House Hotel / Photo x Jessica Kelly

Shopping

Ready to head out to explore the village shops? If you love teas, fancy cups, and teapots you have to stop by the English Rose Tea Shoppe (527 Main St) for a new flavor.

Ellen J Goods (435 Main St) owned by JR and Lynne Brundage is a well-known vintage store in the village where you can find a truly unique piece to bring home. The Brundage’s find old, vintage, torn apart furniture or decor, and turn them into new treasures that will give your home character. Check it out for yourself the next time you’re in town!  

Sift through the clothes at A Lily And A Sparrow (438 Main St) to find the perfect outfit to bring home or head over to Herbalty Cottage (415 Main St) for some new organic herbs, oils, vinegars, and gourmet ingredients to add to your kitchen pantry.

Thumb through the rows and rows of reads at the local book store, The Book Shoppe (519 Main St), to find something new to read. Then, end the day of shopping with a gorgeous bouquet of fragrant fresh flowers from Creekside Floral (509 Main St).

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Dinner

All that lifting of the wallet and walking will have you working up an appetite in no time, so you’ll need somewhere to fight the hangriness when it hits.

Mariachi De Oro

11417 Maple Ridge Rd, Medina, NY 14103 / mariachideoromexicangrill.com

After eating here on more than one occasion, we can safely say this is some of the best Mexican you will ever have. We fully understand that’s a bold statement, but everything from their drinks and guac to the chocolatey, slightly spiced mole sauce and sobes are authentic and full of flavor!

Avanti Pizza & Wood Fired Kitchen

500 Main St, Medina, NY 14103 / iloveavanti.com

If you’re starving, there’s nothing better than a gargantuan slice from Avanti. I needed a word bigger than giant or huge to use because seriously, one slice is a couple bucks and is pretty much an entire pizza. Hats off for their take on the Buffalo chicken slice. It was delicious!  

Harvest

444 Main St., Medina / harvestatbent.com

In the center of downtown this former Bent’s Opera House which was constructed in 1865 is elegant and at the same time cozy. The spectacular (and sparkling) open kitchen adds a great vibe and a chance to see the chefs at work. The kitchen staff has serious creds.  The menu changes regularly based on local fresh ingredients. Add to that a great bar room and The Boutigue Hotel at Bents Opera House upstairs and you have the makings of a terrific evening.

Avanti Pizza & Grill – Medina Road Trip / Photo x Jessica Kelly
Harvest / Photo x Step Out Buffalo
Harvest / Photo x Step Out Buffalo
Harvest / Photo x Step Out Buffalo

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Drinks at Shirt Factory

115 W Center St, Medina, NY 14103 / shirtfactorymedina.com

The Shirt Factory opened up inside the same historical building as the Hart Hotel. Curious about the name? After the Hart House closed down in the early 1900s, the property was snatched up by Robert H. Newell, a business guru that owned a growing high-end shirt business.  He established his business over 86 years inside the historical building throughout the spacious 3 floors where he made custom fit PJs, shirts, and event undergarments for customers. Some of his clientele included big names like John Jacob Astor, Bob Hope, and Winston Churchill. The newly established version of the Hart House Hotel paid tribute to some of the shirt factory visitors and the buildings history by naming the rooms after some of the famous names that got clothing from the building!

Medina Road Trip / Photo x Jessica Kelly
Shirt Factory / Photo x Jessica Kelly

So if you were heading there to get a shirt, don’t. If you’re heading there to have great conversation, food, cocktails, and local to WNY beers, now you’re on the right track!

A couple of local power couples came together to create the sun filled coffee cafe by day turned premium cocktail bar by night known as of the Shirt Factory, and its the perfect addition to this quaint town.

Shirt Factory / Photo x Jessica Kelly
Shirt Factory / Photo x Jessica Kelly

If you’re a sucker for Instagramable drinks and Christmas movie-esque vibes, you’ll love the esthetic and cocktail offerings here. Plus, Scott Robinson, cocktail curator and mixologist for the Shirt Factory, definitely did his research when making the names of his creations.

While the menu has undoubtably changed since 2018, these creative cocktail concoctions we tried on our visit should give you a great idea of what to expect, including “Letters to Santa” made with spiced cranberries and finished with Aperol, a little splash of ginger bitters, bubbly, and Lillet, as well as Zuzu’s Petals”, a frothy gin based drink polished off with sour lemon, cinnamon, sweet vermouth, and blackberry liqueur.

Shirt Factory / Photo x Jessica Kelly
Shirt Factory / Photo x Jessica Kelly
Shirt Factory / Photo x Jessica Kelly
Shirt Factory / Photo x Jessica Kelly

The Shirt Factory also has a selection of sandwiches, veggies, and toasts perfect for picking at while you enjoy a drink. On our visit in 2018, we chose to try the Brie and Bacon Toast with, you guessed it, creamy mild brie, crispy chopped up bacon bites, and caramelized onions on thick toasted Italian bread. Delicious!

Since our visit, The Shirt Factory has narrowed their cocktail concept even further with their new Speakeasy nights. Those participating dress up and receive an email with a password to get in for a night of fun and cocktails. We hear it is pretty cool!


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Day 2


Boozy Brunch at Shirt Factory

115 W Center St, Medina, NY 14103 / shirtfactorymedina.com

On Sundays, Shirt Factory offers a boozy brunch reservations from 10am – 2pm, which is nice because you won’t have to go far from your overnight accommodations to fill that belly. The menu is seasonal and consists of options like breakfast sandwiches, tacos, toast, salads, and more.

Leonard Oakes Estate Winery

10609 Ridge Rd, Medina, NY 14103 / oakeswinery.com

Before heading out of town, make a stop to Leonard Oakes Estate Winery to sample a few wines and bring back a bottle or two for your holiday festivities. As if they read our minds, during the holidays, Leonard Oakes offers Mulled Wine Packs as well as New World and Old World Holiday Packs that are specifically made to be the perfect addition to your gatherings.


A huge thank you to Scott, Alix, and the rest of the team at the Shirt Factory and the beautiful Hart Hotel for making us feel so welcome!

This guide was originally written and published in 2018 and has been updated. Some dishes and products may have changed since.

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Written by <a href="https://stepoutbuffalo.com/author/jessicakelly/" target="_self">Jessica Kelly</a>

Written by Jessica Kelly

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