Looking for wineries in Harbor Springs? Start with Pond Hill Farm and Happy Days & Nights Winery. Both have Harbor Springs addresses, but offer different experiences: a farm visit with food and activities, or a tasting room at a hilltop bed-and-breakfast. For a wider route, consider Crooked Vine in Alanson or Seasons of the North in the Indian River area.
The right plan depends on what you want from the day. Lunch with friends, a tasting for two, and a group celebration each need a different pace. Use the guide below to choose your stops, check the details, and leave time to enjoy them.
Harbor Springs wineries at a glance
| Winery | Location | What you can expect | Check before visiting |
|---|---|---|---|
| Pond Hill Farm | Harbor Springs, north of downtown | Wine, beer and cider tasting, café, farm activities | Café hours and activities for your date |
| Happy Days & Nights Winery | Harbor Springs, on South Pleasantview Road | On-site winery and tasting room at a B&B; walk-ins welcomed | Current tasting hours and arrangements for groups |
| Crooked Vine Vineyard & Winery | Alanson | Red and white wines from sweet to dry, vineyard views and a covered patio | Seasonal opening days |
| Seasons of the North | Indian River area, on M-68 | Wine, beer and hard cider tastings, plus an outdoor wine garden | Current hours and your group’s requirements |
The last two are regional additions, so allow for travel beyond Harbor Springs when planning your day.
Wineries to visit in Harbor Springs
Pond Hill Farm: pair your tasting with a farm visit
Pond Hill Farm is five miles north of downtown Harbor Springs on M-119, at 5699 S. Lake Shore Drive. It is a useful choice when your group wants more than a tasting room.
The farm combines drinks with a café, market, trails and seasonal activities. You can make lunch part of the visit, while guests who are not tasting have other things to enjoy. Its visitor guide explains what is available through the year.
If food and time outdoors matter to your group, make this your main stop. Leave room in the schedule for a meal or walk before heading to another winery.
Happy Days & Nights Winery: a tasting room at a hilltop B&B
Happy Days & Nights combines a bed-and-breakfast with a winery that makes wine on the premises. The property lists its address as 6767 S. Pleasantview Road, Harbor Springs.
You do not need to assume an overnight stay is required. Its wine tasting room page explicitly welcomes walk-ins and says B&B guests receive a complimentary tasting. It directs visitors to its Google listing for updated hours.
Consider this stop if you like the idea of a winery within a lodging property. For a group outing, call 231-526-8100 to discuss your arrival and tasting arrangements. Walk-in access does not mean every group size can arrive without notice.
Nearby wineries for a longer outing
Crooked Vine Vineyard & Winery in Alanson
Crooked Vine Vineyard & Winery is at 8370 Lakeview Road, Alanson. Its tasting selection includes red and white wines across the sweet-to-dry range, and visitors can enjoy vineyard views from a covered patio.
This is worth considering when your group wants to spend time around the vines as well as at the tasting bar. Ask about the wines available that day and tell the staff which styles you usually enjoy.
Check its seasonal schedule before choosing a date. The winery publishes different opening days for summer, fall, winter and spring, so a day that works in July may not work in October.
Seasons of the North in the Indian River area
Seasons of the North lists its location on M-68 in Indian River. Treat it as an extension to your route, rather than a stop in Harbor Springs itself.
Its visitor information lists wine, beer and hard cider tastings, along with an outdoor wine garden in spring through fall. Those choices may suit a group with different drink preferences.
Call 231-548-1280 to confirm your visit time, especially outside the summer season. Build the rest of the itinerary around the hours confirmed for your date.
If you are also considering stops around Petoskey, these wineries in Petoskey, Michigan offer more options for a separate outing or a different route.
How to plan your Harbor Springs wine day
Start with two stops, then decide whether you want a third. This is a planning suggestion, not a fixed tour length: meals, group size, tasting arrangements and travel all affect what fits.
For a day centered on Harbor Springs: consider Pond Hill Farm and Happy Days & Nights. Choose the order after checking both schedules. If lunch is part of the plan, use your meal time to help set the route.
For a vineyard-focused outing: choose a Harbor Springs stop and consider Crooked Vine as your Alanson addition. Leave time to sit and enjoy the setting rather than treating each visit as a quick tasting.
For a wider regional day: consider Seasons of the North if its location and hours fit your onward plans. You do not need to visit every place in this guide to have a full afternoon.
Before booking, settle four details:
- Your group size. Give each winery the total number arriving together, including anyone who will not be tasting.
- Your budget. Ask for current tasting prices, then allow separately for food, bottles and transportation. Confirm what any tour quote includes.
- Your must-have stop. Check availability there first, then build the rest of the day around it.
- Your transportation. Arrange a designated driver who will not drink, or book private transportation before finalizing tasting times.
If anyone needs step-free access or other accommodations, ask about the tasting room, restroom and outdoor areas individually. A patio photo cannot tell you whether the whole visit will work for your group.
Private transportation with Petoskey Wine Tours
Petoskey Wine Tours offers private tours with sedans and Suburbans, professional drivers, personalized plans and door-to-door convenience.
Tell us your preferred wineries, travel date, group size and pickup address. If you are staying in Harbor Springs, ask us to confirm pickup coverage and which stops fit the time you have available.
Before reserving, confirm the vehicle, quote, pickup and return times, and who will arrange winery reservations. Ask how tasting fees and meals are handled so everyone knows what to budget.
Questions about wineries in Harbor Springs
Are the wineries in downtown Harbor Springs?
The two Harbor Springs options covered here are outside the downtown core. Pond Hill Farm is north of downtown on M-119, while Happy Days & Nights is on South Pleasantview Road. Plan transportation between your lodging and the properties.
Can you visit Happy Days & Nights without staying overnight?
Yes. Its tasting room page welcomes walk-ins. Check current tasting hours before going, and contact the property in advance for a group visit.
Which stop has options for people who do not want wine?
Pond Hill Farm offers food and farm activities as well as tastings. Seasons of the North lists beer and hard cider alongside wine. Check the current food and nonalcoholic drink choices if those are important to your group.
Can you visit wineries near Harbor Springs in winter?
There are winter options. Pond Hill Farm describes winter activities in its visitor guide, and Crooked Vine publishes winter opening days. Check each property’s current schedule before choosing a route.
Can Petoskey Wine Tours pick us up in Harbor Springs?
We advertise door-to-door transportation. Share your exact Harbor Springs pickup address and date so we can confirm availability, coverage and timing before you book.
Plan a wine day that fits your group
Choose the places you most want to visit, leave room for food and conversation, and arrange the ride before setting your tasting times.
To discuss a private tour, contact Petoskey Wine Tours or call 231-645-5957. Have your date, group size and pickup location ready, along with any wineries you would like to include.
