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Glen Cove Mansion offers historic buildings, an upscale restaurant and 186 guest rooms. (Photo Credit: Discover Long Island)

About an hour west of Riverhead and 40 minutes east of New York City, Long Island’s Gold Coast makes for the perfect road trip no matter which direction you’re coming from. The North Shore’s historic mansions and museums are glistening with memories from the gilded age and roaring 20’s, and the off season is chance to tour some of these opulent estates free of crowds. Bundle up and enjoy this kid-friendly, dog-friendly day trip itinerary (plus a couple of great options for staying overnight, if you choose).

Avocado toast at Organic Krush is the ideal energizing breakfast. (Photo Credit: Courtesy Organic Krush)

Breakfast at Organic Krush, Roslyn

Begin your Gold Coast day trip with a smart and healthy breakfast. Organic Krush has multiple locations across Long Island. Their restaurant in Roslyn is located just twenty minutes away from Hempstead House at the Sands Point Preserve, our second stop.

Organic Krush has a wide selection of choices like acai bowls, gluten-free baked goods, smoothies, cold-pressed juices, and coffee beverages. They also have a great selection of children’s meals with no nuggets in sight. These include the Buddha Bowl (brown rice, broccoli, and chicken) and Monkey Roll-Up (almond or peanut butter with banana and honey in a wrap with a side of apple slices).

1508 Old Northern Blvd, Roslyn, 516-206-4072

Sands Point Preserve offers guided walks around its miles of grounds. (Photo Credit: Discover Long Island)

Explore Sands Point Preserve

Become lost in nature at the stunning Sands Point Preserve. The preserve and conservancy is home to four lavish mansions on the Guggenheim Estate: Hempstead House, Castle Gould, Falaise and Mille Fleur. The mansions and welcome center are currently closed; this is however, the perfect opportunity to get outside and explore the forest trails, great lawn, and pond area.

Sands Point Preserve features guided nature walks and meditative walks during the winter season. Tickets are available at their gatehouse. In addition, self-guided tours are perfect for families of all ages looking to explore the grounds at their own pace. These include the History Tour, the Bird Watching Tour and Native Wildlife tour. For children, check out the Woodland Playground, and for fido, the dog run is perfect for playtime.

127 Middle Neck Rd, Sands Point, 516-571-7901

The Oheka Castle is closed for tours, but the on-site restaurant is a lovely spot for lunch. (Credit: Phillip Ennis)

Lunch at Oheka Castle

After your hike and trail walk, drive 40 minutes to Oheka Castle in Huntington. While the castle is currently closed for tours, you can have a relaxing and upscale meal and a glimpse inside at the on-site OHK Bar & Restaurant, with lunch beginning at 12pm. Please note that reservations or call ahead seating is required. Indoor and al fresco dining options await, weather permitting.

Menu highlights include the lobster BLT, filet mignon French dip, short rib grilled cheese, penne seafood, and an Asian-style veggie burger. Celebrate the afternoon with their Peanut Butter Brownie Sundae.

Visiting for Valentine’s Day? Oheka Castle also offers romantic overnight packages for two. Valentine’s Day packages include a special prix-fixe menu, long stem roses, champagne, Belgium chocolate covered strawberries and much more.

When mansion tours recommence, they are run daily at 11am by advanced reservation only and are usually followed by coffee, tea, and cookies. Should you wish to tour Oheka Castle from home, they do offer virtual tours

135 West Gate Drive, Huntington, 631-659-1400

Sagamore Hill National Historic Site. (Courtesy Photo)

Hike the Grounds of Sagamore Hill

A drive of less than 20 minutes leads you to Sagamore Hill National Historic Site, which President Theodore Roosevelt called Sagamore Hill home from 1885 until his passing in 1919. While the Theodore Roosevelt Home and Old Orchard Museum are closed due to COVID concerns, the estate nicknamed the “Summer White House” features 80 acres of beautiful landscape to walk about until sunset.

The park grounds, walking paths, and trails are open, including the beach area and Eel Creek bridge, an ideal photography spot. There is currently no fee to visit the grounds of Sagamore Hill, and dogs are welcome as well.

20 Sagamore Hill Rd, Oyster Bay, 516-922-4788

The interior of the Mansion at Glen Cove. (Photo Credit: Discover Long Island)

Dinner at The Mansion at Glen Cove 

Twenty-two minutes west of Sagamore Hill is The Mansion at Glen Cove. The Mansion was originally known as The Manor and was once the country house of John and Ruth Baker Pratt.

Your while family can dine in opulence here: Options on the Prix Fixe menu from executive chef Rodrigo Bernal include a jumbo crab cake, dry sea scallops, Burgundy pear salad and Australian lamb chop.

The Mansion also has 186 guest rooms and suites available Thursday through Sunday, if you want to stay overnight, and a special breakfast and brunch in January for hotel guests. The hotel will also host a kid-friendly “Breakfast with Princess” on January 31 and February 20 featuring an elaborate brunch, music, crafts and more for your favorite little princess. Advanced reservations are required ($35 for adults, $20 for children).

200 Dosoris Ln, Glen Cove, 516-671-6400