A long weekend in Canandaigua, New York, in the Finger Lakes, was one of those. We were celebrating my dad’s birthday, and it ended up being the perfect mix of lake time, great food, and doing exactly what we felt like.
We made the drive up from Maryland, starting along I-83 before heading further north. If you’re planning a similar route, I’ve already mapped out some of my favorite stops in my guide to where to eat along I-83 from Baltimore to Harrisburg, which makes breaking up the drive a lot easier.
What made this trip even better was the balance—we spent time together as a family, but still had space to do our own thing throughout the weekend.
If you’ve explored places like Nelson County, Virginia or Williamsburg, and you’re looking for something a bit more luxe outside of the mountains, this feels like a natural next step.
Where to Stay: The Lake House on Canandaigua
We stayed at The Lake House on Canandaigua, and it completely shaped the experience.
Being right on the lake made everything easier—morning coffee, bike rides, pool time, and getting out on the water were all right there.
Since we were traveling as a group, having our own hotel rooms made a big difference. We could spend time together when we wanted, but also break off during the day—whether that was biking, fishing, or just sitting by the water.
If you’ve stayed somewhere like Getaway House in North Carolina, this has a similar feel but certainly more luxe and less isolated—relaxed, design-forward, and built around slowing down.
Day 1: Corning Stop + Arrival in Canandaigua
Stop in Corning, NY
On the drive up, we stopped in Corning Museum of Glass, and it was 100% worth it.
As someone who finds glassblowing fascinating, this was a super interesting museum to me.
Lunch at The Butcher’s Son
After the museum, we grabbed lunch at The Butcher’s Son
The chicken sandwich was crispy, cheesy, and exactly what you want mid-road trip—messy in the best way.
Dinner: Kix on Main
Once we got to Canandaigua and settled in, we headed to Kix on Main for dinner.
This was a great first-night spot—casual, good energy, and an easy way to ease into the weekend. The buffalo cauliflower was a standout.
Day 2: Coffee, Biking, Boat Day & the Best Meal of the Trip
Morning Coffee: The Dalai Java
We started the day here—quick, easy, and exactly what we needed to get going.
If you’re someone who plans trips around coffee stops, this felt similar to some of the spots I’ve found in Portland, Maine—simple, local, and consistently good.
Mid-Morning: Bike Ride Along the Lake & Through Town
We spent part of the morning biking along the lake and through town—flat, scenic, and super relaxed.
If you enjoy slower, scenic destinations like Lakeside, Michigan or Long Beach Island, this has a very similar feel.
Afternoon: Boat Rental + Tubing
We rented a boat as a group, and this was easily one of the highlights of the trip. My dad picked up some serious speed and really whipped us around on the tube.
Lunch: Macri’s Deli
Quick, simple, and really solid sandwiches. Great to eat on the boat.
Dinner: FLX Table (Best Meal of the Trip)
This was, without question, the best meal of the weekend.
FLX Table is a tasting menu experience that feels intentional without being overly formal.
The standout for me was the farmer’s board and the house-made butters—duck fat, brown butter, turmeric, and even strawberry—which completely elevated the experience.
From there, the meal built into seasonal dishes that were balanced, well-executed, and never overcomplicated.
Nothing felt rushed, and the pacing made it easy to actually enjoy the meal.
If you plan trips around food, similar to how I approach weekends like my St. Louis food guide, this is absolutely worth building your night around.
Day 3: Coffee, Markets, Kayaking & Lake Life
Morning Coffee: Working Class Coffee
A great, simple start to the day.
Canandaigua Farmers Market
Quick stop, but worth it.
Midday: Bike Ride + Kayaking
The morning kayak was one of the most peaceful parts of the trip. My fiancee and I love to kayak, but my parents don’t get the chance all that often, it was nice to paddle away from the shore and just drift a bit.
Lunch: The Sand Bar at The Lake House
Casual, lakefront, and very easy to spend a few hours here.
Afternoon: Pool Time
Pool, drinks, lake views—nothing else needed.
Dinner: Rose Tavern
Another great dinner this trip—elevated but still relaxed.
Day 4: One Last Slow Morning + Drive Home
Morning: Coffee at The Lake House
Slow start, one last bike ride, and soaking in the lake views.
Drive Home Stops
We kept it casual on the way back:
- Joseph’s Wayside Market
Fresh, local produce - The Sawmill Restaurant
Comfort food that hits - Soul Full Cup
One last stop before finishing the drive
More Travel Guides You’ll Love
If you’re planning more trips like this, here are a few that follow a similar style:
- Relaxed escapes:
- Mid-Coast, ME
- Tilghman Island, MD
- Food-focused weekend trips:
- Telluride, CO
- Asheville, NC
- Scenic and nature-driven getaways:
- Shenandoah National Park
- Nelson County, VA
- Floyd, VA
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