On Saturday, October 10, three groups each hold their own event in Chester. The Sugar Loaf Fall Festival opens in the hamlet at 10 a.m. The free "Chalk it up!" sidewalk drawing festival starts at the same hour at the Erie Depot on Winkler Place. The Chester Public Library opens its downstairs book sale on Kings Highway an hour earlier, at 9. None of the three is tied to the others, and their closing times are spread across the whole day.
The village events wrap up early and the hamlet keeps going until evening. So the order you visit them decides how much of the day you actually get. If you begin at the 1915 railroad station in the village and finish at the brunch house Valkyrie built inside an early-1900s train station in Sugar Loaf, the timing works almost exactly.
The Village Side Closes First
Here are the hours that set the route, as each organizer has posted them:
- 9 a.m. to 4 p.m.: Chester Public Library book sale, downstairs at 1784 Kings Highway
- 9 a.m. to 1 p.m.: Saturday hours listed for the Erie Railroad Station Museum, May through October
- 10 a.m. to 1 p.m.: "Chalk it up!" at the Erie Depot Train Station, 19 Winkler Place
- 11 a.m. to 1 p.m.: Book bedazzling at the library
- 7:30 a.m. to 2 p.m.: Brunch service at Valkyrie Brunch House, 1398 Kings Highway, Thursday through Sunday
- 2 to 3:15 p.m.: Teen mini pumpkin painting party at the library
- 10 a.m. to 5 p.m.: Sugar Loaf Fall Festival, free admission
Both depot events end at 1 p.m. and the brunch kitchen closes at 2. The festival runs until 5. Arriving in Sugar Loaf at 10 gives you the hamlet at its most crowded hour, and you'd likely miss the chalk event in the village. Going the other direction puts each event in its own window.
Start at the 1915 Station
The Erie Railroad Station at 19 Winkler Place was built in 1915. The Chester Historical Society says Orange County leased the station to the society for 99 years in July 1991, and the restored building opened to the public as a museum on June 12, 1999. The Orange Heritage Trail runs right past it. According to the Town's 2026 comprehensive plan draft, the Goshen to Chester section was built on the old Erie Mainline right-of-way and opened on June 7, 1997, with the 1915 station at its Chester end.
That's why "Chalk it up!" is held here. The Town calls it a free sidewalk drawing festival at the depot next to the Heritage Trail, and its rain date is Sunday, October 11. The Historical Society says the museum is used for trail events. Its listed Saturday hours, 9 a.m. to 1 p.m. through October, fall on the same morning as the chalk event. October 10 is one of the last Saturdays left in that season. The hours appear on an undated page, so call the Historical Society before you plan around them.
A Stop on Kings Highway
The library at 1784 Kings Highway comes next because its hours give you the most room. The book sale runs until 4 p.m. on Saturday and comes back Sunday, October 11, from 11 a.m. to 4 p.m. If you stop by after the chalk event, you can still catch the end of book bedazzling, which runs from 11 to 1.
The one real conflict of the day is the teen mini pumpkin painting party from 2 to 3:15 p.m. It overlaps the early afternoon at the festival. A household with a teenager who wants to go can split the day: drop off at the library, head to Sugar Loaf, and come back afterward. The festival is open until 5, so the afternoon in the hamlet doesn't have to end when the party does.
The Second Station Serves Brunch Until Two
Valkyrie Coffee Roasters opened its flagship roastery on Main Street in downtown Chester on February 1, 2020. On September 10, 2025, it opened a second location at 1398 Kings Highway in Sugar Loaf. The company says it turned an early-1900s train station and caboose into an international fusion brunch house there, with the same pastries and drink specials as the Main Street shop plus a brunch menu served Thursday through Sunday from 7:30 a.m. to 2 p.m.
This October is the brunch house's second fall festival weekend. Its 2 p.m. close is why the route ends in Sugar Loaf. If you finish the village by lunchtime, you get to the old station in the hamlet with time to eat before the kitchen closes, and you can walk into the festival afterward. If you go to the festival first, you'll be at a brunch counter in the busiest part of the day.
The Hamlet After Lunch
The Sugar Loaf Chamber of Commerce bills the festival as two days of artisan crafts, live music, food and drinks, and family activities. It's held at the Sugar Loaf Art & Craft Village on Kings Highway. One calendar listing gives the address as 1371 Kings Hwy, and the Warwick Advertiser's October 1 roundup gives it as 1365. Either way, it's the stretch of Kings Highway that runs through the middle of the hamlet.
Most of the permanent shops sit within a few addresses of each other. The Chamber's 2026 walking map and its directory list them this way:
Romers Alley and 1371 Kings Highway
- Bliss Co-op, in Romers Alley at 1371 Kings Highway
- Collage, 1371 Kings Hwy, Building 5
- Eureka Books & More, 3 Romers Alley
1373 to 1381 Kings Highway
- Cachet Home Market, 1373 Kings Highway
- Merrily Paper and Rosner Soap, both at 1375 Kings Highway
- The Candle Shop, 1378 Kings Highway
- Lightclub Curiosity Shoppe, 1379 Kings Highway
- Vulgaris Herbs, 1381 Kings Highway
Past the Center
- Nick Zungoli Exposures Gallery, 1357 Kings Highway
- Bostree at 56 Wood Road and Jimmy'Z Jewelry at 62 Wood Road
The Chamber notes on the map that each store sets its own hours and asks visitors to check individual websites. The festival dates don't guarantee every door will be open from 10 to 5. The same map marks four parking areas but doesn't name them or say how many cars they hold, and the Chamber hasn't posted a shuttle plan for 2026. Chester Police logged 14 hours of "Sugar Loaf Fall Festival Details" in their October 2025 monthly report. That gives a sense of how much traffic the weekend brings. If you get there after lunch, the morning crowd will have had a few hours to spread out.
When the Festival Closes at Five
At 5 p.m. the hamlet shifts from festival to dinner. Sugar Loaf Taphouse at 1368 Kings Highway describes itself as an American grill open seven days a week. Cancun Inn at 1396 Kings Highway, next door to the brunch house, lists Saturday hours of 11:30 a.m. to 10 p.m. The Chamber's map also lists Tin Barn Brewing at 62 Kings Highway Bypass for beer, food and live music.
Sunday Is the Backup Plan
If Saturday doesn't go to plan, three of these events have a second day. The festival runs again Sunday, October 11, from 10 to 5. The library book sale reopens from 11 to 4. If it rains Saturday, "Chalk it up!" moves to Sunday. On Sunday, the depot museum's Saturday hours are the only part of the route you can't get back.
After that weekend, the calendar slows down. The library and the Town are hosting a children's trick-or-treat visit to Town Hall at 1786 Kings Highway on Thursday, October 29, from 10:45 to 11:45 a.m. Children gather first in the library program room and then walk next door. The Chester Historical Society's Dutch Treat Annual Dinner is set for Tuesday, November 17, at 6 p.m. The location hasn't been announced yet.
If you own a home between Winkler Place and the Sugar Loaf depot and are thinking about how its location and history should be presented to buyers, Rebecca A Bank offers a private valuation built on that kind of local detail. Schedule a Consultation.
