Upstate Getaway Giveaway...The Tarrytown Weekend You Should Already Be Planning!
- Hudson Valley Happenings
- 1 day ago
- 7 min read
Updated: 8 hours ago
Spring has arrived in the Hudson Valley, and Tarrytown is the answer to the question you have been asking since February. What does a real upstate weekend look like? It looks like this. May 1 through 3, one of the best craft fairs in the Northeast takes over the grounds of Lyndhurst Mansion, and we built an entire weekend around it, a historic estate hotel, a waterfront dinner on the Hudson, a bottle of small-batch bourbon made here in the Hudson Valley, and a night out in Dobbs Ferry that does not know when to quit. We are giving the whole thing away to one winner. But whether you enter or not, this is the weekend blueprint worth bookmarking.
May 1st-3rd
Where The Season Begins & The Bar Is Set
Spring Crafts at Lyndhurst runs May 1 through 3, and few events open the season with this kind of authority. More than 200 artists, and makers spread across the grounds of Lyndhurst Mansion, each one bringing work that feels considered and personal. Ceramics with real weight. Textiles you want to run your hands across. Woodwork that still carries the shape of the tree it came from. Jewelry made by someone who took their time getting it right. This is not a flea market with ambitions. It is a curated gathering of people who take the work seriously, set against one of the most impressive estates in the Hudson Valley.
Lyndhurst does a lot of the heavy lifting before you even find the first booth. The estate opens toward the Hudson, wide lawns sloping gently to the river, the mansion rising behind you like something preserved from a more deliberate time. Artrider Productions has been running this event for decades, and the experience reflects that, organized without feeling corporate, scaled without losing intimacy. You move through it at your own pace, stop when something earns your attention, double back without guilt. The grounds give you room to breathe in a way that most events simply cannot.
Some pieces will stay with you. Some will be gone if you come back on day three. That urgency is part of what makes Spring Crafts at Lyndhurst worth planning around — not just for the work itself, but for the setting, the scale, and the particular feeling that comes from being somewhere the season genuinely begins. The Hudson Valley has plenty of craft fairs. This is the one people mark the calendar for.
At a Glance:
Spring Crafts at Lyndhurst Mansion
635 S Broadway, Tarrytown, NY
Instagram: @artridercrafts Website: artrider.com
May 1 through 3, 2026
Friday, from 10-5
Saturday, from 10-6
Sunday, from 10-5
Parking: On-site parking at Lyndhurst (fills quickly)
Good to Know: Over 200 juried artists, spread-out grounds on the Hudson, best selection early, worth taking your time walking the full estate
The Hudson River Estate Redefining the Upstate Getaway
Tarrytown House Estate sits on 26 acres along the Hudson River, and something shifts the moment you arrive. The noise drops off, the space opens up, and the pace changes without asking permission. This is a working historic estate. Federal-era architecture, manicured grounds rolling toward the river, the kind of setting that takes a second to fully register. You are not checking into a hotel. You are stepping into somewhere that has been holding this view for two centuries and it shows immediately.
The buildings carry genuine estate character that no amount of renovation budget can manufacture. But the experience is uncomplicated in the best way. Mornings start with light coming off the Hudson, breakfast without urgency, and time that feels genuinely unstructured. You walk the grounds, find a quiet spot without trying, and realize you have nowhere else you need to be. It is the rare kind of place that does not require an itinerary to justify itself, the grounds alone earn the stay.
Tarrytown House Estate is the kind of Hudson River hotel that changes how the whole weekend registers. Not because it overdelivers on amenities or tries to be everything. Because 26 acres of Hudson Valley landscape, a historic estate, and two mornings with reason to rush have a way of making everything else feel slower and better by comparison. Two nights here is the difference between a day trip and something you actually soak up.
At a Glance:
Tarrytown House Estate
49 E Sunnyside Ln, Tarrytown, NY
Instagram: @tarrytownhouseestate Website: tarrytownhouseestate.com
Open year-round
Check-in: 4:00 PM Check-out: 11:00 AM
Parking: On-site parking available for guests
Good to Know: 26-acre Hudson River estate, historic buildings with modern rooms, quiet grounds ideal for walking, close to Lyndhurst and downtown Tarrytown
Built for the Water, Designed for the Night
The Sailhouse sits on the historic Tarrytown waterfront, right beside the Washington Irving Boat Club marina, where the site’s original story still lingers. The new version honors that history without leaning on it. Everything here was built with intention. Dutch Delft tile nods to Tarrytown’s Dutch roots. Rattan lighting, a fireplace, and a bar framed like a residential bookcase anchor the room. Round mirrors quietly reference porthole windows. Velvet curtains and candlelight soften the space, while the coastal brightness keeps it from ever feeling heavy. Nothing about it feels themed. It feels considered, from the baseboards up, built around the idea that people remember how a place felt long after they forget what they ordered.
Step outside and the entire pace shifts. The patio opens straight to the Hudson, the tiki bar runs alongside it, and the marina sits right there. You can dock, dine, and drink without breaking stride. A summer stage brings live music to the water’s edge, and as the sun drops, the Mario Cuomo Bridge lights up in the distance. At some point, the table goes quiet. The menu stays in that same lane, New American, seasonal, well executed without needing explanation. Drinks come fast, the music builds, and somewhere between the second round and the bridge lighting up, the night settles into itself.
Waterfront dining in Tarrytown doesn’t get better than this. The Sailhouse works as a destination on its own and somehow fits even better as part of a full weekend. You come in with a plan, a reservation, a table by the water. The night moves past that pretty quickly.
At a Glance:
The Sailhouse
238 Green Street, Tarrytown, NY
Instagram: @thesailhousetarrytown Website: thesailhousetarrytown.com
Phone: (914) 332-0517
Parking: Private lot on site plus public lot next door
Hours: Monday & Wednesday – Thursday: 11:00 AM – 10:00 PM
Friday – Saturday: 11:00 AM – 12:00 AM
Tuesday: Closed
Good to Know: A short walk from Tarrytown Metro North Train Station Tiki bar, summer stage with live music, dock and dine available
Field to Glass. Nothing in Between.
Hillrock Estate Distillery operates out of Ancram, New York, about an hour north of Tarrytown. It It surrounds a restored 1806 Georgian house overlooking rolling fields and the distant Berkshire Mountains. Everything happens on the Estate. The grain is grown there, floor malted there, pot distilled, aged, and hand bottled without ever leaving the grounds. Grain-to-glass is a term the spirits industry uses loosely. At Hillrock, it is not just a marketing line. It is the actual process, start to finish, continuing a centuries-long Hudson Valley distilling heritage.
The Double Cask Bourbon spends more than five years aging in two American oak casks. First a number three char, then a number four. It is then bottled in bond at 100 proof. Bottled in bond is not a casual designation. One distillation season, one distiller, one distillery, aged under federal government supervision for a minimum of four years. What Hillrock produces under those standards is dark amber, rich, and built in layers that reveal themselves slowly. Warm vanilla and gingerbread on the nose. Dark chocolate, honey-roasted nuts, and a buttered toffee finish that lingers long after the glass is empty. It drinks like something that was never in a hurry to be finished.
This is what Hudson Valley bourbon tastes like when someone refuses to cut corners on any part of it. Hillrock is not trying to compete with Kentucky. It is doing something distinctly its own, grain-forward, terroir-driven, and rooted in a region that was producing whiskey long before most of the names people recognize today. The winner takes a bottle home. It will not last long, and that is entirely the point.
At a Glance:
Hillrock Estate Distillery
408 Pooles Hill Rd, Ancram, NY
Instagram: @hillrockestatedistillery Website: hillrockdistillery.com
Open for tours and tastings (select days)
Hours vary, reservations recommended
Parking: On-site parking available
Good to Know: Field-to-glass distillery, all grain grown on estate, Double Cask Bourbon aged 5+ years
Best Reason to Miss Your Train.
Hudson Social lives inside the restored Dobbs Ferry train station, and the building earns its place before you even sit down. The bones are all there. The architecture, the scale, the sense that this space has always been somewhere people passed through and stayed longer than they planned. The restoration kept what mattered and made the rest work for a room that runs from breakfast through last call. High ceilings. An open layout. A dual-level space that handles an intimate dinner and a packed Friday night with equal ease. There is a private loft upstairs, and a patio outside that faces the Hudson, with an outdoor bar that stays busy as soon as the weather turns.
Dinner moves into drinks without much transition. The menu is modern American and well executed, the kind of food that works as a full meal or something to pick at between rounds. The cocktail program is serious without being overworked. Live music builds with it, the room fills in around you, and conversations stretch well past the point where anyone is checking the time. The patio and outdoor bar carry their own energy, the crowd leans in, and the bar knows the difference between a good pour and a great one. It’s a place people come back to weekly and wish they had found sooner.
The night doesn’t taper off at Hudson Social. It just keeps finding reasons to continue. Another round, another song, one more thing somebody wanted to say. For a weekend that started at a craft fair on the grounds of a Hudson Valley mansion and moved through a waterfront dinner and two nights on the river, this is the right place to close it out. Loud enough to feel alive. Good enough to mean it.
At a Glance:
Hudson Social
11 Station Plaza, Dobbs Ferry, NY
Instagram: @hudsonsocialndobbsferry Website: hudsonsocial.com
Open daily
Hours vary by day
Parking:
Free parking in lot, ask hostess for parking pass, plus nearby municipal lots and street parking
Good to Know: Located inside a restored train station, waterfront patio with outdoor bar, live music, strong late-night crowd, easy transition from dinner into drinks
One winner. Every stop on this list. A $500 voucher to Spring Crafts at Lyndhurst, two nights at Tarrytown House Estate with breakfast each morning, a riverside dinner for two at The Sailhouse, a bottle of Hillrock Double Cask Bourbon, and dinner for two at Hudson Social. The itinerary is already built. The only thing missing is your name on it.
Head to our latest Instagram post to enter.
Never Stop Winning!
HVH Team
