The Rhinebeck Sheep and Wool Festival fills the Dutchess County Fairgrounds this weekend, 53 minutes from Clove Creek Cabin. Kingston spends the same two days restaging the British burning of 1777 in its own streets, and Hunter Mountain, eleven minutes from the cabin, closes its fall festival with a costume weekend. If you came up last weekend, our October 10–11 guide covered Hunter’s Oktoberfest round.
Below: every pick on our events calendar for October 17–18, grouped by drive, with hours and admission from each organizer’s own page, checked on October 14. Organizers can change prices on the day, so check the official page before you go.
Every pick this weekend
Within an hour of the cabin
| Event | When | Admission | From Clove Creek |
|---|---|---|---|
| Colors in the Catskills: Costume Takeover, Hunter Mountain | Sat 11–6, Sun 11–5; Skyride from 9 | Free admission and parking; VIP $41 / $89 | ~11 min |
| Subversive Oktoberfest Weekend, Catskill | Fri–Sun; German band Sat 3–6 | Not listed | ~40 min |
| Catskill Farmers Market, Water Street | Sun 10–1 | Not listed | ~40 min |
| The Burning of Kingston, uptown Stockade District | Sat 10–5 camps, battles 3:30; Sun 5K 9, finale 3 | Most events free; Senate House tours $7 | ~43 min |
| New York State Sheep & Wool Festival, Rhinebeck | Sat–Sun | $15 presale, $18 at the gate; 11 and under free | ~53 min |
| Headless Horseman Hayrides & Haunted Attractions, Ulster Park | Fri–Sun, 7–9 pm | See the organizer | ~55 min |
One to two hours from the cabin
| Event | When | Admission | From Clove Creek |
|---|---|---|---|
| Beacon Sloop Club Pumpkin Festival, Beacon waterfront | Sun | Free; free sails, weather permitting | ~1 h 18 min |
| Big Apples Fest, Heritage Financial Park, Wappingers Falls | Sat 10–4 | Parking $10 advance, $15 on the day | ~1 h 23 min |
| Fishkill Farms Fall Harvest Festival, Hopewell Junction | Sat–Sun; corn maze 10–5 | Corn maze $5 | ~1 h 29 min |
| The Great Jack O’Lantern Blaze, Van Cortlandt Manor, Croton-on-Hudson | Evenings from 6 | From $24; advance only | ~1 h 51 min |
About three hours from Manhattan
| Event | Where | When | Admission |
|---|---|---|---|
| 5th Annual Witch Walk & Dance | Saratoga Springs | Sat 2–9 | $30 wristband ($35 at the door), to animal charities |
| Saratoga’s 9th Annual Wing Off | Saratoga County restaurants | Sat 11–4 | $2 wing samples |
| BOOP! The Musical | Proctors, Schenectady | Through Sun | Proctors box office |
| Naumkeag Pumpkin Show | Stockbridge, MA | Wed–Sun 5–9 | $32 adults, $15 ages 3–15; timed tickets |
| Hyde & Shriek! Candlelit Ghost Tours | Hyde Hall, Cooperstown | Sat evening | Tickets on Eventbrite |
| Things That Go Bump in the Night | Fenimore Farm, Cooperstown | Sat, tours 5:30–8 | $20; $17.50 members |
| Rhythm Future Quartet | Fenimore Farm, Cooperstown | Sun 3:00 | $30; students and youth $10; under 6 free |
About five hours from Manhattan
| Event | Where | When | Admission |
|---|---|---|---|
| SLOB Fest 2026 | 41 Lakefront Hotel, Geneva | Sat 1–5 | $40 early-bird through Oct 15; designated drivers $10 |
| Empire Brick Con | Corning Museum of Glass | Sat–Sun | Free with museum admission; 17 and under free |
| High Peaks Harvest Festival | Saranac Lake | Sat; market 10, festival 12–4 | Not listed |
| 63rd Brooktondale Apple Festival | Brooktondale Community Center | Sat 10–3 | Not listed |
| Oktoberfest at Colloca Estate Winery | Sterling | Sun from 11:30 | Not listed |
The Rhinebeck Sheep and Wool Festival
The New York State Sheep & Wool Festival takes over the Dutchess County Fairgrounds in Rhinebeck on Saturday and Sunday. It brings fiber vendors, sheep shows, herding demonstrations and workshops, plus a fleece show and sale.
Tickets. $15 in advance (plus an online fee) or $18 at the gate, each good for one day. Children 11 and under are free.
The show ring. The Black & White sheep show runs Saturday at 2 and Sunday at 10.
Getting there. Rhinebeck is 53 minutes from the cabin, so you can spend the morning in the barns and be back on the deck by dark.
A day in the wool barns, an evening of reenacted gunfire in Kingston, and the hot tub between them.
Kingston burns again
The Burning of Kingston runs Thursday to Sunday in the uptown Stockade District, marking the day in 1777 when British troops set the town on fire. Saturday is the big day. The British camp at the Senate House, the colonial militia at the DAR House and the civilians on the Old Dutch Church grounds all run from 10 to 5. The militia meets the British advance at Frog Alley at 10:15, and the street battles begin at 3:30, with gunfire and cannon. Most of the program is free. Senate House tours are $7 for adults.
On Sunday, the Capital to Capital 5K traces the refugees’ route from Kingston to Hurley from 9 (register ahead for the timed run), and the weekend closes at 3 with Songs of America at the Old Dutch Church, sung by the Bard Conservatory’s vocal program.
Hunter’s costume weekend, eleven minutes away
Colors in the Catskills ends its three-weekend run at Hunter Mountain with the Costume Takeover. Admission and parking are free, and the hours are the same as the earlier rounds: Saturday 11 to 6, Sunday 11 to 5, with the Scenic Skyride opening at 9. If you were there for the first weekend, our October 10–11 weekend guide covered Hunter’s Oktoberfest round; this is the finale, and the Catskills peak foliage is still worth the Skyride up.
Saturday. Probable Cause plays at 1, 2 and 4, with keg rolling and kids’ steinholding at noon, the costume contest and parade at 3 and steinholding at 5.
Sunday. Becca Frame and the Tall Boys at 1, 2 and 4, steinholding at noon and the costume contest and parade at 3.
The lift. The $89 VIP package includes a Skyride ticket and an express line; the $41 VIP is a shirt, a mug and a beer, without the lift.
Forty minutes from the cabin, Subversive Malting & Brewing in Catskill holds its Oktoberfest weekend Friday through Sunday, with bratwurst, spaetzle and Bavarian boards. On Saturday it releases its Mountain Märzen with a gravity keg tapping, a German band plays the beer garden from 3 to 6, and The Lager Goblin takes over after. On Sunday, the Catskill Farmers Market is on Water Street from 10 to 1, with one Sunday left in its season after this one.
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The Beacon Sloop Club’s Pumpkin Festival is on the Beacon waterfront on Sunday. Admission is free. There are two solar-powered music stages, one of them for kids, food and craft vendors, and river and environment groups. The club’s sloop, the Woody Guthrie, takes guests out on free sails from Beacon Harbor, weather permitting.
On Saturday across the river, the Hudson Valley Renegades hold their second Big Apples Fest at Heritage Financial Park in Wappingers Falls, 10 to 4: live music, seasonal beers, games, inflatables and apples. Parking is $10 in advance or $15 on the day. Fishkill Farms in Hopewell Junction keeps its harvest weekends going, with the $5 corn maze open 10 to 5, Sons of Hudson on the cider porch Saturday and Bourbon Sprawl on Sunday.
After dark, two Halloween walks. The Great Jack O’Lantern Blaze lights Van Cortlandt Manor in Croton-on-Hudson with more than 7,000 hand-carved jack-o’-lanterns, from about 6 each evening. Tickets start at $24 and are sold in advance only, with nothing at the gate. Closer to the cabin, Headless Horseman Hayrides in Ulster Park runs its hayride, corn maze and haunted houses Friday to Sunday, 7 to 9 per the state tourism listing.
Three hours out: Saratoga, the Berkshires, Cooperstown
Saratoga Springs is busy on Saturday. From 2 to 9, the 5th Annual Witch Walk & Dance brings more than 500 costumed witches to downtown Saratoga Springs to walk, dance and raise money for animal charities; the Witch Way Market in Congress Park runs from 10 to 2. The wristband is a $30 donation, or $35 at the door. Earlier, from 11 to 4, the 9th Wing Off sends you around Saratoga County restaurants for $2 wing samples, and your vote picks the county’s best wings. Part of the proceeds goes to the American Cancer Society. In Schenectady, BOOP! The Musical ends its Proctors run on Sunday. Proctors is 87 minutes from the cabin, so it’s an easy evening out.
Cross into Massachusetts for the Naumkeag Pumpkin Show in Stockbridge, where jack-o’-lanterns light the historic gardens Wednesday to Sunday, 5 to 9. Tickets are timed: $32 for adults and $15 for kids 3 to 15, with an earlier, quieter hour from 4 to 5.
Cooperstown has three picks, and it makes one of the better day trips in upstate NY for adults. On Saturday night, Hyde Hall runs its candlelit Hyde & Shriek! ghost tours, and Fenimore Farm leads lantern tours through its darkened village from 5:30 to 8 for $20 ($17.50 for members). On Sunday at 3, the Rhythm Future Quartet plays gypsy jazz in the spirit of Django Reinhardt at Fenimore Farm: $30 general admission, $10 for students and youth, under 6 free.
Five hours out: Finger Lakes and the Adirondacks
Saturday in Geneva, SLOB Fest gathers the Seneca Lake breweries at the 41 Lakefront Hotel from 1 to 5, with live music and food. Early-bird general admission is $40 until Thursday, October 15, at 5. In Corning, Empire Brick Con fills the Corning Museum of Glass with LEGO builds all weekend. It’s free with museum admission, which is free for anyone 17 and under, and the ticket is good for two days. Brooktondale’s 63rd Apple Festival runs 10 to 3 on Saturday, with apple pies and crisps, a cake wheel, a quilt raffle and the Easy as Pie 5K.
Up north, Saranac Lake’s High Peaks Harvest Festival starts with the farmers market at 10, then runs artisans, local food, craft drinks and live music from noon to 4. On Sunday, Colloca Estate Winery in Sterling holds an Oktoberfest on the lake from 11:30, with polka from the Krazy Firemen Band and German food.
Where to stay
Clove Creek Cabin sits between Hunter and Phoenicia: eleven minutes from the costume weekend, 43 from Kingston and 53 from Rhinebeck. It has two bedrooms for up to four guests, an indoor fireplace, and a hot tub and sauna on the deck. Check dates for Clove Creek on Airbnb.
Blue Heron in Tannersville is a two-bedroom for up to four guests, about a five-minute walk from Tannersville’s restaurants and shops, with a fire pit, and pets are allowed. Check dates for Blue Heron on Airbnb.
FAQ
When is the Rhinebeck Sheep and Wool Festival in 2026?
The New York State Sheep & Wool Festival is Saturday and Sunday, October 17–18, 2026, at the Dutchess County Fairgrounds in Rhinebeck.
How much are Sheep and Wool Festival tickets?
$15 in advance plus an online convenience fee, or $18 at the gate. Each ticket is good for one day, and children 11 and under are free.
Is Hunter Mountain’s fall festival free this weekend?
Yes. Colors in the Catskills’ Costume Takeover on October 17–18 has free admission and parking. The Skyride is part of the $89 VIP package; the $41 VIP has no lift.
Which festivals near the Catskills are free this weekend?
Hunter Mountain’s Costume Takeover, the Beacon Sloop Club Pumpkin Festival and most of the Burning of Kingston program are free to enter. Empire Brick Con is free with museum admission. Food, drinks and rides cost extra.
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