Top 10 Best Reasons To Take a Girl’s Trip To Canandaigua

Come along on a girl’s trip to Ontario County! I’m going to take you through the top 10 best reasons to take a Girl’s Trip to Canandaigua. This picturesque slice of the Finger Lakes region in Upstate New York is the perfect mix of natural beauty, adventure, and charm. My last Finger Lakes visit was back in 2018 for a travel bloggers conference, and I knew I had to return. What better excuse than a girls’ getaway? This time, my friend Lindsay and I focused on Canandaigua, a city that blends small-town warmth with vibrant energy—ideal for hiking trails, scenic wine tours, and unwinding in the autumn air.

Ontario County is steeped in history, from the legacy of the Haudenosaunee (Iroquois) people to landmarks like the courthouse where Susan B. Anthony’s trial made history. Women’s rights are a cause close to my heart, so visiting that courthouse will be a meaningful stop. Beyond history, Canandaigua is a haven for outdoor lovers, foodies, and wine enthusiasts alike. It’s the kind of place that wraps you in its charm and invites you to savour the scenery, local arts, and adventure—a must-visit for your next girls’ trip! 

I think that Canandaigua should be on any travel lover’s list. Canandaigua has this magnetic blend of natural beauty and small-town charm (although it’s a city) that feels both vibrant and peaceful. There’s so much to explore, from the wineries and nature to the cute downtown. Canandaigua is a perfect spot for a girls’ trip, blending just the right mix of relaxation, adventure, and appeal. 

And in autumn, the Finger Lakes are just gorgeous! So sit tight, and let’s get into this Ontario County Girls trip itinerary.

How Do You Get To Canandaigua? 

Getting to Canandaigua from Toronto is an easy 3 to 3.5-hour drive, covering about 260 kilometres (160 miles). Cross the U.S.-Canada border at the Queenston-Lewiston Bridge near Niagara Falls, then follow I-90 East and Route 332 South straight into Canandaigua.

From Belleville or Kingston, it’s about a 3 to 4-hour drive (250-280 km/155-175 miles). Cross the border at the Thousand Islands Bridge near Gananoque, then follow I-81 South, Route 104 West, and Route 21 South into town. 

For a non-driving option, fly into Rochester, NY (30 minutes from Canandaigua) or take a bus or train from Toronto, though these options take longer and may include transfers.

If you’d like to read about the time I have spent in Rochester, only a half hour away from Canandaigua, check out

Head To The Rochester Fringe Festival For An Amazing Time!

and

10+ Best Places in Rochester New York To Play, Eat and Drink

Best Reasons To Take a Girl’s Trip to Canandaigua 

Back to our girl’s trip! We found that Ontario County combines natural beauty, adventure, and a deep-rooted sense of history for nerds like us, making it a perfect spot for relaxation and exploration. I have the top 10 best reasons to take a girl’s trip to Canandaigua. Let’s jump in! 

 

#1 Visit the Seneca Art & Culture Center at Ganondagan State Historic Site

We are kicking off our girls’ trip with a visit to the Seneca Art & Culture Center at Ganondagan State Historic Site in Ontario County—it’s the perfect mix of meaningful and memorable. This 17,300-square-foot center honours the Haudenosaunee (Iroquois) contributions to art, culture, and society with interactive exhibits, a stunning film sharing the Iroquois Creation Story, and thoughtfully designed spaces that offer a chance to reflect on the enduring presence of the Haudenosaunee people.

Then we stepped outside and walked the Earth is Our Mother Trail, where we learned about the deep relationship between the Seneca people and the plant world. These trails weave through the living landscape of Onondowahgah, the land of the Seneca, offering a space to appreciate the significance of their connection to nature. It’s a peaceful, eye-opening experience perfect for a meaningful day of bonding, reflection, and connection with the land and its history.

Finally, we explored the Seneca Bark Longhouse just behind the centre. This remarkable structure is a full-size replica of a traditional 17th-century Seneca home, where we gained a deeper understanding of Haudenosaunee’s daily life and community. I found it to be a unique opportunity to step back in time and experience the architecture, stories, and culture that continue to inspire and educate visitors today. This experience was perfect for a meaningful day of bonding, reflection, and connection with the land and its history.

#2 Take In A Can’t-Miss View

The Finger Lakes are known for being beautiful, but especially in autumn with the fall foliage and canopies, there are a couple of spots to stop and take in an incredible view!

Harriet Hollister Spencer State Recreation Area

Since I’m always looking for jaw-dropping views that feel like a secret hideaway, Harriet Hollister Spencer State Recreation Area is it. Perched above Honeoye Lake, this hidden gem offers panoramic views that feel like a well-kept secret. When the fall leaves are at their peak, it’s breathtaking. Pack a thermos and a snack for a peaceful pause in your adventure.

Ontario County Park at Gannett Hill

At over 2,200 feet, this park boasts some of the highest, most expansive views in the area. Perfect for a picnic or a quick hike, it’s a must-stop for those epic Finger Lakes vibes, especially at sunset.

County Road 12 Scenic Overlook

A Finger Lakes road trip isn’t complete without this quick stop for unreal views of Canandaigua Lake. Sunrise or sunset here is next-level gorgeous—the kind of memory that sticks with you long after the trip.

#3 Take Your Adventures To New Heights

If you’re ready to add some adrenaline to your adventure, Bristol Mountain’s Aerial Adventures is where it’s at! This tree-top obstacle course in the heart of the Finger Lakes is perfect for anyone looking to challenge themselves and have an unforgettable morning. With seven different courses of varying difficulty, you’ll climb, swing, zip, and balance your way through the forest, all while enjoying incredible views of the surrounding hills. Whether you’re a first-timer or a seasoned thrill-seeker, there’s a course for everyone to conquer.

I am always one to zip on that zipline. I love them. And any sort of physical challenge. What makes this spot so fun is how it combines adventure with nature. It’s not just about pushing yourself physically (though your muscles might feel it later!); it’s also about soaking up the beauty of the forest and the sense of accomplishment when you hit that final zipline. If you’re travelling with friends, it’s the perfect activity for cheering each other on, laughing at your attempts to cross wobbly bridges, and making memories you’ll be talking about for years.

Heads up! Bristol Mountain’s Aerial Adventures is an epic challenge, but it’s not without risks. Safety is key when you climb, swing, and zip through the trees. Listen to the staff, use the gear properly, and know your limits. Adventure comes with a little risk, but be safe. Don’t go in over your head, and you’ll have an unforgettable (and safe!) experience.

#4 Finger Lakes Wine Tasting

If you’re planning a girls’ trip to the Finger Lakes, make sure to add a stop at the Heron Hill Tasting Room to your itinerary. Heron Hill is more than a tasting—it’s an experience. The tasting room is perched in such a stunning spot, a renovated 100-year-old barn offering gorgeous views of the surrounding hills and Keuka Lake. Whether you’re wine-savvy or just love sipping with your friends, their tasting flights are a fun way to explore the variety of Finger Lakes wines.

We started with their Classic Chardonnay, which was beautifully balanced—rich and buttery with just the right amount of oak. It had this subtle vanilla note. Next, we tried the Unoaked Chardonnay, which was so bright and refreshing! It’s all about the crisp apple and citrus flavours, and it felt like it would be perfect for a warm day on the patio.

For something different, the Blaufränkisch caught our attention. This bold and earthy red was accompanied by notes of dark cherry and a hint of spice. The standout was their Lady of the Lakes Bubbly Red—a lightly sparkling red that’s fruity and fun to drink. It’s like the party starter of their collection, ideal for toasting with your best girls.

Between the wine, the views, and the welcoming vibe, it’s the kind of place that feels like the highlight of the day (note from me – EVERYTHING in this trip is a highlight. I can’t just pick one).

#5 Barrel Sauna Relaxation

We were looking to melt away stress and treat ourselves on this girls’ trip, so the barrel sauna at Willowbrook Spa in Canandaigua was the ultimate indulgence. Located almost right on the water on the serene grounds of The Lake House, this unique and shared experience blends relaxation with nature in the most luxurious way. The cozy, rounded wooden sauna feels intimate and inviting, and as soon as you step inside, it’s just an escape!

The gentle sauna heat works wonders, easing muscle tension and giving our skin that post-sauna glow. We did three cycles of sauna heat, a cool shower and a round with a face mask. Even more magical is the view—just imagine looking out onto the peaceful lake or the spa’s lush surroundings! 

After the session, we took a beat to cool off outdoors and sipped on herbal tea in that blissed-out state. What a perfect way to reset recharge, and it made our trip to Canandaigua feel extra special.

#6 Stay at Chalet of Canandaigua

The best place to stay? The Chalet of Canandaigua is a dream getaway in the heart of Ontario County. This boutique B&B feels like a home away from home, offering serene views, cozy fireplaces, and easy access to local trails and wineries. Staying here is all about relaxing and recharging in a peaceful, picturesque setting. With just three elegant suites and a large, enjoyable common room, the Chalet feels intimate and special. The entire house can also be rented out, so it’s a cool spot for a large family gathering or a huge girl’s getaway!

I had the Woodsview Suite. It was very cozy with its warm, inviting decor, luxurious king-sized bed, and private sitting area. The real highlight? The forest views right outside the window—it’s like waking up in a woodland fairy tale. It’s also closest to the kitchen, so if you’re an early riser and want that fresh coffee first, you’re right there!

This suite is perfect if no one is upstairs in the balcony suite, as the Woodsview Suite is on the main floor, and the Balcony Suite is on the second floor, directly above. I am not a very heavy sleeper by any stretch, so earplugs would have gone a long way! 

#7 Hire A Private Chef at The Chalet of Canandaigua

Hiring Chef Keith Hillock at the Chalet of Canandaigua takes your stay to a whole new level of indulgence. Imagine enjoying a private, gourmet dining experience tailored just for you, all without leaving the cozy luxury of the B&B. Chef Keith is known for crafting incredible meals using fresh, local ingredients that highlight the best of the Finger Lakes region. He also knows a thing or two about feeding ravenous hungry as he’s the executive chef for the Rochester Red Wings.

Whether it’s a romantic dinner, a celebratory feast, or just a treat-yourself moment like what Lindz and I did, having a personal chef prepare and serve your meal is an unforgettable touch. Plus, he can accommodate your preferences or dietary needs, making the experience completely personalized. Since I don’t eat shellfish, he prepared Chilean sea bass for me! 

He will pair your dinner with a bottle of local wine and cider, and you’ve got an evening that feels straight out of a dream!

#8 Indulge in the Food and Craft Beer scene

The Finger Lakes region isn’t just about stunning lakes and rolling vineyards—it’s a foodie and beer lover’s dream come true! With a mix of farm-to-table dining, creative craft breweries, and a deep appreciation for local ingredients, this area knows how to serve up unforgettable flavours.

Whether you’re sipping on a crisp NY lager (lagers are my favourites of anyone wants to buy me a round), indulging in a gourmet meal inspired by the seasons, or kicking back at a cozy pub with a flight of small-batch brews, the Finger Lakes food and beer scene is all about celebrating what makes this region special. Trust me, every bite and sip here comes with a side of appeal and a taste of the local passion.

New York Beer Project (Victor, NY)

Step into history at this beautifully recreated turn-of-the-century beer hall inspired by NYC’s iconic Atlantic Garden circa 1870. With crystal chandeliers, the space is as impressive as the drinks and food. Enjoy a craft beer or non-alcoholic option alongside a hearty entrée, knowing you’re part of a story celebrating American brewing heritage. Here, Lindsay and I each got a flight to try. And because it was seasonal, the drunken pumpkin was a complete delight. The New York Beer Project is a feast for your eyes and taste buds!

BeeHive Brew Pub (Canandaigua, NY)

Beehive Brew Pub is your quintessential neighbourhood spot—welcoming, laid-back, and buzzing with good vibes. Just off the main strip, it’s the kind of place where the service is friendly, and the beer list is always on point. They feature a fantastic selection of craft brews, with a special focus on New York State beers, making it easy to sip your way through the region’s best. Whether you’re stopping in for a pint or a bite, this cozy pub makes you feel right at home with its no-fuss, classic charm. It’s not trying to be flashy—it’s just consistently good. The tuna melt was comfort on my plate! It’s a must-try.

Rose Tavern at The Lake House (Canandaigua, NY)

The Rose Tavern is on the list of places to eat for dinner. Located at the chic Lake House on Canandaigua, this New American restaurant showcases the best local ingredients in a seasonal, rustic menu. The ambiance is upscale yet relaxed, and the dishes are crafted with care, thanks to close partnerships with local growers. Lindsay and I shared an appetizer of beef carpaccio, and then I went with a portion of pasta for my main.

Pair your meal with a perfectly curated drink, and enjoy the cozy, lakeside vibes for a memorable dining experience. This was where we ate after our incredible barrel sauna experience.

#9 Pay Homage To Susan B. Anthony and The Suffrage Movement

Canandaigua isn’t just a pretty spot in the Finger Lakes; it’s a cornerstone in the story of American suffrage. If you’re curious about Susan B. Anthony, she stood trial in 1873 in Canandaigua at the courthouse after being arrested for the bold act of voting in the 1872 presidential election. At that time, only men were allowed to vote. She argued passionately in court that voting was a basic right for all citizens. Despite her strong case, she was found guilty and slapped with a $100 fine – which she flat-out refused to pay. All for the crime of voting while being female.

It’s a place to remember that our rights today are built on the courage and defiance of trailblazers like Susan B. Anthony.

#10 – Explore Downtown Canandaigua

Beyond the vineyards and lake life, Canandaigua has a vibrant arts and food scene to dive into. Main Street in Downtown Canandaigua is filled with artisanal shops, farm-to-table restaurants, and historic sites, giving you plenty to explore. 

There are some great coffee shops where you can grab a cuppa, like Dalai Java or North Star Coffee, but if tea is more your passion, be sure to visit Good Life Tea. If you’re shopping for a small gift or something for yourself, check out Wildflower and Blue Door Boutique.

Have a sweet tooth? Sweet Expressions is waiting for you!

While many of these activities do cost money, a nice wander downtown is a free things to do in Canandaigua.

Whether kayaking on the lake, at an aerial adventure, relaxing in Willowbrook, the Spa at The Lake House or exploring the boutiques and restaurants along Main Street, Canandaigua is the perfect spot to unwind and enjoy life’s simple pleasures for a Finger Lakes girls weekend getaway.

With its stunning lake views, you and your friends can kick back and enjoy the best the Finger Lakes region has to offer.

There’s a little bit of everything here, making Canandaigua the perfect balance of laid-back and lively for an unforgettable girls’ trip! I hope this Top 10 list helps fuel the imagination for a girlfriend’s weekend getaway ideas in Upstate NY!

I bet you’d enjoy your time in Canandaigua as much as I did! If you’re looking for accommodations there, feel free to browse this map of the area.

KathrynAnywhere is a participant in the Stay22.com Affiliate Program. We may receive a commission if you make a purchase after clicking on one of these links.

 

I was hosted by Visit Finger Lakes and asked to produce this blog post as part of my stay in exchange for compensation. Lindsay and I really did have a lovely time. I will definitely go back!