If you are searching for things to do in Montgomery, NY, you have come to the right place. The Village of Montgomery sits at the heart of Orange County in the Hudson Valley, roughly 70 miles north of Manhattan — close enough for a day trip, far enough to feel like a different world. And at the center of it all is Clinton Street: a half-mile stretch of historic storefronts, independent restaurants, boutique shops, and genuine small-town charm that makes this village one of the Hudson Valley's best-kept secrets.
Whether you are a local looking for your next favorite spot or a visitor planning a weekend escape from the city, this guide covers everything Clinton Street and the surrounding area have to offer — from morning coffee to sunset balloon rides.
Morning: Coffee and Breakfast on Clinton Street
Start your day at Java Blue Coffee, a neighborhood favorite known for its fresh juices, smoothies, espresso drinks, and house-baked goods. They open at 6am on weekdays and 7am on Saturdays, making them the earliest option for caffeine seekers. Pair your latte with one of their made-to-order breakfast sandwiches and you are set for the morning.
If you prefer a sit-down breakfast, Iron Cafe at 59 Clinton Street (on the corner of Bridge and Clinton) is a Montgomery institution. Open since the early days of the village's dining renaissance, Iron Cafe serves creative breakfast sandwiches, pastries, and specialty cold foam drinks. They open at 6am Monday through Friday, 7am Saturday, and 7am Sunday — with a cozy atmosphere that makes lingering over coffee feel natural.
For something more substantial, PBF Cafe at 94 Clinton Street serves breakfast and brunch with a unique Polish-Brazilian twist. Family-owned by Anna and Leo, this newcomer (recently relocated from Walden) has quickly become a village staple. Try the Fusion Omelette or their Brazilian-style pão de queijo alongside a proper caipirinha at weekend brunch.
Shopping: Boutiques, Antiques, and One-of-a-Kind Finds
Clinton Street is a shopper's paradise if you appreciate independent, curated retail over big-box chains. Here are the highlights:
Steadfast Heart (122 Clinton Street) — A women's boutique offering carefully selected clothing, shoes, accessories, and gifts that blend modern style with timeless quality. Owner Tara has built a loyal following since opening in 2025, creating a space where shopping feels personal and intentional. Open Tuesday through Friday 10am–5pm, Saturday 10am–4pm.
The Last Optical (77 Clinton Street) — Not your average eyewear shop. The Last Optical is a luxury eyewear destination carrying designer frames from Lindberg, Mykita, ic! Berlin, Face à Face, Garrett Leight, SALT. Optics, and more — brands you will not find at chain optical stores. We also offer comprehensive eye exams and our signature Dry Eye Spa treatments. Even if you are not in the market for glasses, stop in to see the space — it was designed to feel more like a boutique than a doctor's office.
Up-Scale Re-Sale (110 Clinton Street) — An eclectic consignment and resale shop with a carefully curated eye. Open Tuesday through Friday 10am–6pm and Saturday 10am–5pm, it is the kind of place where you walk in for five minutes and emerge an hour later with treasures you did not know you needed.
Montgomery Antique Center — A multi-dealer antique center that has been a Clinton Street anchor for years. Whether you collect vintage furniture, estate jewelry, or mid-century curiosities, this is worth a browse.
Lunch and Afternoon Dining
Montgomery's restaurant scene has quietly become one of the best in Orange County, with multiple acclaimed options within a few blocks of each other.
The Table (73 Clinton Street) — New American cuisine with a cocktail bar that has become a community gathering place. Their seasonal lunch menu runs Thursday through Saturday from 11am to 2:30pm, with Sunday brunch from 10am to 2pm. The Apple Panini is a local favorite. Craft cocktails are excellent.
Wildfire Grill (74 Clinton Street) — Farm-to-table dining in a fine-casual atmosphere. Every single item on the menu is made in-house, from appetizers to desserts, using locally sourced ingredients. Consistently excellent and a perennial favorite on TripAdvisor.
Antonio's Family Restaurant (118 Clinton Street) — A neighborhood staple serving both Mexican and Italian cuisine. Open Monday through Saturday 11am–8pm and Sunday 12–7pm. They deliver, too — perfect if you are staying at one of the local B&Bs and want a cozy night in.
Flor De Maguey — Authentic Mexican cuisine crafted from scratch with fresh, farm-to-table ingredients. An abundance of vegetarian options makes this a great choice for groups with varied dietary preferences.
Fine Dining and Evening
When the sun starts to set and you want something elevated, Montgomery delivers.
88 Charles Street — Modern Italian fine dining with expertly crafted cocktails, premium steaks, fresh seafood, and an intimate atmosphere. Reservations recommended. Call (845) 457-9850. The kind of restaurant that makes you forget you are in a small town.
Ward's Bridge Inn — Housed in a restored historic inn, this is Montgomery's longest-standing fine dining establishment and the #1 restaurant on TripAdvisor with over 200 reviews. Steaks, seafood, poultry, and seasonal specials in a setting that honors the building's heritage.
Borland House Inn (130 Clinton Street) — A private five-course dining experience available as an add-on when booking a stay at this historic 1780s bed and breakfast. Chef Anna Frumes trained professionally in France and brings a refined farm-to-table approach. Weekend public brunches feature guest favorites like the Chicken and Waffle Sandwich.
Pubs and Nightlife
For a more casual evening, Clinton Street has two beloved neighborhood pubs:
Copperfield's Kildare Pub — An Irish pub with character. Wednesday burger specials are a local tradition. Cold pints, good company, and the kind of atmosphere where strangers become friends.
RoseMary's Pub and Grub — Live music nights, bingo, rotating drink specials, and satisfying pub fare. The kind of place that gives a small town its soul.
Outdoor Adventures Near Montgomery
Montgomery is surrounded by natural beauty, and outdoor activities are some of the best things to do in the area.
Hot Air Balloon Rides — Montgomery is one of the premier hot air balloon destinations in the Northeast. Above the Clouds offers rides seven days a week, launching from fields just outside the village. Floating over the Hudson Valley at sunrise or sunset is an unforgettable experience — and the views of the Shawangunk Ridge and Catskill Mountains are spectacular.
Kayaking the Wallkill River — The Wallkill River Water Trail runs right through Montgomery, with a public launch at Riverfront Park. A popular 30-minute paddle takes you downstream to City Winery — where you can dock, have lunch, and taste wine before paddling back. Suitable for beginners.
Winding Hills Park — This Orange County park offers a 4.8-mile hiking loop (moderate difficulty), camping with 51 sites, boating, fishing, and picnicking in summer. In winter, conditions permitting, there is ice skating, ice fishing, and snowmobile trails. A true four-season destination just minutes from Clinton Street.
Otterkill Trail — A peaceful walking trail that follows the Otterkill Creek through wooded areas. Perfect for a morning stroll or an afternoon with the dog.
Wine, Spirits, and Live Music
City Winery Hudson Valley (23 Factory Street) — Just steps from Clinton Street, City Winery occupies a stunning 22-acre property with a fully functioning winery, restaurant, tasting room, and concert venue. Open Wednesday through Sunday, it hosts nationally touring musicians alongside wine tastings and farm-to-table dining. The terrace overlooking the vineyards is one of the most beautiful spots in Orange County.
Shawangunk Wine Trail — Thirteen wineries comprise this trail that winds through the rolling hills surrounding Montgomery. Spend a day visiting two or three, and you will understand why the Hudson Valley is emerging as a serious wine region.
Magnanini Winery — A family-owned winery with an Italian restaurant on-site. Wine tastings, live music on weekends, and a rustic charm that feels authentically Hudson Valley.
History and Culture
Montgomery Village Museum (142 Clinton Street) — A village-run museum housed in a historic building right on Clinton Street. The displays cover all aspects of Montgomery's history — from its founding in 1810 through its development as a commercial center. Free admission. A quick but fascinating stop that gives context to everything you see walking the street.
Borland House — Even if you are not staying overnight, the Borland House itself is worth admiring from the street. Built in the 1780s with a striking Greek Revival addition in the early 1800s, it is listed on the Haunted History Trail of New York State. The 12-foot ceilings, period details, and sunset views from the upper floors are remarkable.
Seasonal Events
Summer Concert Series — Every Thursday evening from June through August, the Montgomery Community Recreation Center hosts free outdoor concerts from 6:30 to 8:30 PM. The 2026 season kicks off June 17. Bring a blanket, grab takeout from one of the Clinton Street restaurants, and enjoy live music under the stars.
Farmers Markets — Seasonal markets bring local produce, baked goods, honey, and artisan crafts to the village throughout the growing season.
Holiday Events — Montgomery's downtown comes alive during the holiday season with tree lightings, shop open houses, and themed brunches at the Borland House (including murder mystery and psychic brunches).
Where to Stay
Borland House Inn (130 Clinton Street) — A 5-star bed and breakfast in a historic Greek Revival home. Spa and wellness amenities, gourmet breakfast included, and you are literally steps from every restaurant and shop on this list. The perfect home base for a weekend exploring Montgomery and the Hudson Valley.
Getting Here
Montgomery is located in Orange County, NY — approximately 70 miles north of Manhattan via I-87 (the New York State Thruway). The drive takes about 75 minutes from Midtown without traffic. The village is also easily accessible from Newburgh, New Paltz, Middletown, and Beacon. Street parking is free throughout the village.
Plan Your Visit
Clinton Street rewards those who take their time. Our recommendation: arrive mid-morning, start with coffee, browse the shops, have a long lunch, explore the outdoor options in the afternoon, and finish with dinner and wine. You will leave wondering why you had not visited sooner — and already planning your return.
And if your eyes need attention while you are here, stop by The Last Optical at 77 Clinton Street. Whether you need a comprehensive eye exam, want to browse our collection of luxury designer frames, or are curious about our Dry Eye Spa treatments, we would love to welcome you. Call (845) 606-4220 or book an appointment online.
The Last Optical — 77 Clinton Street, Montgomery, NY 12549. Luxury eyewear, comprehensive eye exams, and dry eye spa treatments in the heart of the Hudson Valley.