Hudson Highlands gateway with a revived arts district and 3.2 miles of riverwalk.
Tips on renting in Peekskill
Getting Around
What to Pack
Must-Try Activities
Smart Spending Tips
An hour north of Grand Central, Peekskill occupies a curved bay where the Hudson widens into Peekskill Bay, sheltered from the main river channel by a rocky peninsula. The town had a long industrial decline but has spent the last decade rebuilding around its waterfront — the Charles Point Marina, the Factoria complex, and River Outpost Brewing are the visible signs of that. Hudson Valley MOCA (Museum of Contemporary Art) anchors the arts district a few blocks from the river. The result is a town that feels genuinely alive without feeling packaged, which is harder to find in the Hudson Valley than it used to be.
The Hudson River Connection
Peekskill’s 3.2-mile riverwalk spans nearly the entire Hudson shoreline and connects to Riverfront Green Park and Peekskill Landing. Charles Point Marina has 96 slips and is the main departure point for watercraft. Kayak rentals and guided paddling trips on Peekskill Bay are available seasonally through local outfitters — the bay’s calmer waters make it suitable for beginners. Scenic Hudson Park at the northern end of the riverwalk provides additional shoreline access and Hudson Highlands views. Bear Mountain State Park is 14 miles south and connects to the Long Path trail network.
Where to Stay
Peekskill’s vacation rental market is smaller than Beacon or Tarrytown but growing, with a mix of apartments in historic downtown buildings and standalone homes in the residential neighborhoods above the waterfront. For the best access to the riverwalk, marina, and arts district, look for listings near the waterfront district or within a 10-minute walk of Charles Point. Larger groups benefit from full houses with off-street parking. The waterfront area is walkable for dining and trail access; a car helps for Bear Mountain or Westchester County day trips. Two-night minimums on weekends are standard.
What to Do
Hudson Valley MOCA (1701 Main St) runs rotating contemporary exhibitions in a purpose-built gallery space and is free on certain days. The Paramount Center for the Arts (1008 Brown St) programs live music, comedy, and film year-round in a restored historic theater. The Peekskill Riverwalk is the easiest 3+ miles of flat walking on the Hudson — suitable for strollers, bikes, and dogs. Bear Mountain State Park (14 miles south) has the Appalachian Trail, Perkins Memorial Tower views, and a seasonal lake swimming area. The weekly farmers market runs downtown on Saturdays.
Food and Local Rhythm
River Outpost Brewing Co. at Charles Point Marina is the town’s best riverside hang — an expansive deck, seasonal raw bar, and small-batch ales brewed on-site, including the well-regarded Callooh Callay oyster gose. Birdsall House on N Division Street is the local gastropub standby, with a back patio and rotating tap list. Fin & Brew on the waterfront handles fresh seafood and river views. For morning coffee before the riverwalk, Bean Runner Café on South Division has been the anchor local café for years. The Abbey Inn & Spa’s restaurant, Apropos, serves the most formal dining option in the area.
Best Time to Go
Late spring through early fall is Peekskill’s best window — the riverwalk is fully operational, the brewery deck is open, and the Marina is active. June and September hit a sweet spot between peak summer crowds and shoulder-season quietness. October brings foliage and the town fills with day visitors from Westchester. The arts district operates year-round; winter visits focused on museums and indoor dining are viable but cold. Summer weekends are warm and active, though not as crowded as Beacon or Cold Spring.
Practical Rental Advice
Metro-North’s Hudson Line serves Peekskill (60–70 minutes from Grand Central), with the station about a 10-minute walk from the waterfront. Drivers should confirm off-street parking, especially near the marina district on summer weekends. Pet-friendly listings exist and Peekskill’s trails and parks are dog-welcoming with leashes. Check listings for air conditioning — essential for July and August in the river valley. Two-night minimums are standard for weekends; mid-week availability is generally good.
Quick tips before you book
- River Outpost Brewing deck fills on summer evenings — arrive early or reserve ahead.
- The Peekskill Riverwalk is stroller- and dog-friendly; confirm your rental’s proximity.
- Bear Mountain State Park requires a car or rideshare — about 25 minutes south on Route 9.
- Metro-North stops at Peekskill station, roughly 60–70 minutes from Grand Central.
- Check air conditioning for July–August stays; the river valley runs warm and humid.
Browse all Peekskill vacation rentals on Lake.com, or explore more Hudson Highlands getaways nearby.
Frequently Asked Questions
Ready to see what Peekskill has to offer? Let’s tackle some of the burning questions you might have as you plan your visit!
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Peekskill has a growing short-term rental market, smaller than Beacon or Tarrytown but expanding in line with the town’s waterfront revival. Listings typically include apartments near the arts district and waterfront, plus full houses in residential neighborhoods above the river. Weekend availability is generally better than in Cold Spring, but October foliage weekends can still book out 3–4 weeks ahead. Check Lake.com for current listings and rates.
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River Outpost Brewing (Charles Point Marina, Peekskill) is located directly on Peekskill Bay at the marina complex, with an expansive deck overlooking the Hudson River. The brewery produces small-batch ales and seasonal specialties — the Callooh Callay oyster gose and barrel-aged offerings are among the highlights. The menu runs seasonally with a raw bar, BBQ, and waterfront fare. Best enjoyed on a summer evening when the deck is at capacity. Confirm current hours before visiting.
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Bear Mountain State Park is approximately 14 miles south of Peekskill on Route 9W, about 20–25 minutes by car. The park includes Perkins Memorial Tower (panoramic Hudson Highlands views), Appalachian Trail access, Hessian Lake swimming in summer, and extensive hiking trails. No direct public transit from Peekskill — a car or rideshare is needed. A vehicle fee is charged on summer weekends; check the Palisades Interstate Park Commission website for current rates before your visit.
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Peekskill works well for families, particularly those with older children interested in outdoor activity. The 3.2-mile riverwalk is stroller- and bike-friendly. Hudson Valley MOCA runs programming for younger visitors. Bear Mountain, 14 miles south, has swimming, picnic areas, and easier hiking trails well-suited to children. The town has an active farmers market on Saturdays and several family-accessible casual restaurants. Confirm fenced yard or outdoor space if traveling with toddlers.
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Yes, Metro-North’s Hudson Line stops at Peekskill station, approximately 60–70 minutes from Grand Central Terminal. The station is about a 10-minute walk from the waterfront district and arts area. Trains run frequently on weekends. Once in Peekskill, the riverwalk, MOCA, Birdsall House, and River Outpost Brewing are all accessible on foot from the station. A car helps for Bear Mountain and Westchester day trips.
